Diaminotriazine compounds and their use as herbicides

ABSTRACT

The present invention relates to diaminotriazine compounds and to their use as herbicides. It also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation. 
     
       
         
         
             
             
         
       
         
         
           
             wherein 
             p is 1 or 2; 
             q is 0, 1, 2 or 3 provided that p+q is 1, 2, 3 or 4; 
             Q is inter alia a chemical bond, O, S(O) m , CR q1 R q2 , NR q3 , C(O), C(O)O, 
             Ar is phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R A    
             R a  is inter alia hydrogen, halogen, OH, CN, amino, NO 2 , C 1 -C 6 -alkyl, etc; 
             R b  is inter alia halogen, OH, CN, amino, NO 2 , C 1 -C 6 -alkyl, etc.; 
             R 1  and R 2  are inter alia H, OH, S(O) 2 NH 2 , CN, C 1 -C 6 -alkyl, etc; 
             X is a radical selected from the group consisting of CR 3 R 4 R 5 ,
           phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R Ar ;   NR 3a R 3b ,   OR 3c ,   S(O) k R 3d , k being 1, 2 or 3;
 
and including their agriculturally acceptable salts.

This application is a National Stage application of International Application No. PCT/EP2015/058692 filed Apr. 22, 2015. This application also claims priority under 35 U.S.C. §119 to European Patent Application No. 14165565.4, filed Apr. 23, 2014.

The present invention relates to diaminotriazine compounds and to their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation. U.S. Pat. No. 3,816,419 describes 4-haloalkyl or 4-haloalkenyl-2,4-diaminotriazines and their use as herbicides. Similar compounds are known from U.S. Pat. No. 3,932,167.

DE 197 44 711 describes herbicidally active 2,4-diamino-1,3,5-triazine compounds, which carry a group A-Z in the 6-position, where A is alkylene and Z is a carbocylic or heterocyclic radical.

DE 198 30 902 describes amino-chloro-triazine compounds and their use as herbicides.

EP 0545 149 describes 6-trifluoromethyl-1,3,5-triazine compounds and their use as intermediates for crop protecting agents.

EP 0 336 494 and WO 91/13065 describe triazine compounds and their use as herbicide. None of the disclosed examples of theses documents anticipate the compounds of the present invention.

However, the herbicidal properties of the known triazine type compounds are not always entirely satisfactory.

Earlier filed WO 2014/064094 describes 2-(o-fluorophenyl)amino-6-aminotriazine compounds having herbicide activity.

Earlier filed EP 13176634.7 describes 2-(hetaryl)amino-6-aminotriazine compounds having herbicide activity.

Earlier filed EP 14162309.01 (unpublished) describes further (o-fluoro-2-phenyl)diaminotriazine compounds having herbicide activity. It is therefore an object of the present invention to provide compounds having improved herbicidal action, in particular good herbicide activity at low application rates. Moreover, the herbicides should be sufficiently compatible with crop plants for commercial utilization.

These and further objects are achieved by diaminotriazine compounds of formula (I), defined below, and by their agriculturally suitable salts.

Accordingly, the present invention relates

A diaminotriazine compound of formula (I)

-   -   wherein     -   p is 1 or 2;     -   q is 0, 1, 2 or 3 provided that p+q is 1, 2, 3 or 4;     -   Q is a chemical bond, O, S(O)_(m), CR^(q1)R^(q2), NR^(q3), C(O),         C(O)O, CR^(q1)R^(q2)—O, S(O)_(m)NR^(q3) or C(O)NR^(q3),         -   wherein         -   m is 0, 1 or 2;         -   R^(q1), R^(q2) are hydrogen, halogen or C₁-C₄-alkyl;         -   R^(q3) is H, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,             (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl,             (C₁-C₆-alkyl)sulfonyl, where the aliphatic parts of the 6             aforementioned radicals are unsubstituted, partly or             completely halogenated;     -   Ar is phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5         radicals R^(A) which are selected from the group consisting of         halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl,         C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl,         (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,         where the aliphatic and cycloaliphatic parts of the 22         aforementioned radicals are unsubstituted, partly or completely         halogenated and where the cycloaliphatic parts of the last 4         mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,         phenyl, phenyl-C₁-C₆-alkyl, phenylsulfonyl, phenylaminosulfonyl,         phenylaminocarbonyl, phenyl(C₁-C₆-alkyl)aminocarbonyl,         phenylcarbonyl and phenoxycarbonyl,         -   wherein phenyl in the last 8 mentioned radicals are             unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or             different substituents selected from the group consisting of             halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy             and C₁-C₆-haloalkoxy,         -   it being possible that R^(A) are identical or different;     -   R^(a) is selected from the group consisting of hydrogen,         halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl,         (C₁-C₆-alkyl)-carbonyloxy, where the aliphatic and         cycloaliphatic parts of the 14 aforementioned radicals are         unsubstituted, partly or completely halogenated;     -   R^(b) is selected from the group consisting of halogen, OH, CN,         amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl,         C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl,         (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,         where the aliphatic and cycloaliphatic parts of the 22         aforementioned radicals are unsubstituted, partly or completely         halogenated and where the cycloaliphatic parts of the last 4         mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,         for q=2 or 3 it being possible that R^(b) are identical or         different;     -   R¹ is selected from the group consisting of H, OH, S(O)₂NH₂, CN,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₃-C₆-cycloalkyl)-carbonyl,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl,         (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkylamino)carbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl,         di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where         the aliphatic and cycloaliphatic parts of the 15 aforementioned         radicals are unsubstituted, partly or completely halogenated,         -   phenyl, phenyl-C₁-C₆-alkyl, phenylsulfonyl,             phenylaminosulfonyl, phenylaminocarbonyl,             phenyl(C₁-C₆-alkyl)aminocarbonyl, phenylcarbonyl and             phenoxycarbonyl,         -   wherein phenyl in the last 8 mentioned radicals are             unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or             different substituents selected from the group consisting of             halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy             and C₁-C₆-haloalkoxy;     -   R² is selected from the group consisting of H, OH, S(O)₂NH₂, CN,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₃-C₆-cycloalkyl)-carbonyl         C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl,         (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl,         (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl and         (C₁-C₆-alkoxy)sulfonyl, where the aliphatic and cycloaliphatic         parts of the 15 aforementioned radicals are unsubstituted,         partly or completely halogenated,         -   phenyl, phenylsulfonyl, phenylaminosulfonyl,             phenylaminocarbonyl, phenyl(C₁-C₆-alkyl)aminocarbonyl,             phenyl-C₁-C₆ alkyl, phenoxy, phenylcarbonyl and             phenoxycarbonyl,         -   wherein phenyl in the last 9 mentioned radicals is             unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or             different substituents selected from the group consisting of             halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy             and C₁-C₆-haloalkoxy;     -   X is a radical selected from the group consisting of         -   CR³R⁴R⁵,         -   phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5             radicals R^(Ar)         -   which are identical or different;         -   NR^(3a)R^(3b),         -   OR^(3c) and         -   S(O)_(k)R^(3d) with k being 0, 1 or 2,     -   wherein     -   R³ is selected from the group consisting of H, halogen, OH, CN,         C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the aliphatic and         cycloaliphatic parts of the 9 aforementioned radicals are         unsubstituted, partly or completely halogenated;     -   R⁴ is selected from the group consisting of H, halogen, CN,         C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;     -   R⁵ is selected from the group consisting of halogen, CN,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₃-C₆-cycloalkenyl and         C₁-C₆-alkoxy-C₁-C₆-alkyl, where the aliphatic and cycloaliphatic         parts of the 7 aforementioned radicals are unsubstituted, partly         or completely halogenated;     -   R⁴ and R⁵ together with the carbon atom to which they are         attached form a moiety selected from the group consisting of         carbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, three- to         six-membered saturated or partially unsaturated heterocyclyl,         and the moiety >C═CR^(x)R^(y), where R^(x) and R^(y) are         hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;     -   R^(Ar) selected from the group consisting of halogen, OH, CN,         amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl,         C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl,         (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,         where the aliphatic and cycloaliphatic parts of the 22         aforementioned radicals are unsubstituted, partly or completely         halogenated and where the cycloaliphatic parts of the last 4         mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,     -   R^(3a), R^(3b), R^(3c) or R^(3d) are independently of one         another are selected from the group consisting of H, CN,         S(O)₂NH₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₃-C₆-cycloalkyl, (C₃-C₆-cycloalkyl)-C₁-C₆-alkyl,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)-carbonyl,         (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl,         (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-alkylamino)sulfonyl,         di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where         the aliphatic and cycloaliphatic parts of the 15 aforementioned         radicals are unsubstituted, partly or completely halogenated,         -   phenyl, phenylsulfonyl, phenyl-C₁-C₆ alkyl,             phenylaminosulfonyl, phenylcarbonyl and phenoxycarbonyl,             wherein phenyl in the last 6 mentioned radicals is             unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or             different substituents selected from the group consisting of             halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy             and C₁-C₆-haloalkoxy, or     -   R^(3a), R^(3b) together with the nitrogen atom, to which they         are bound, form an N-bound, mono- or bicyclic heterocyclic         radical, which may have 1, 2, 3 or 4 further heteroatoms which         are selected from N, O and S, which is unsubstituted or         substituted by one or more identical or different substituents         selected from the group consisting of halogen, CN, NO₂,         C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy,         one of R^(3a), R^(3b) may also be OH, C₁-C₆-alkoxy,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy         C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,         where the aliphatic and cycloaliphatic parts of the 7         aforementioned radicals are unsubstituted, partly or completely         halogenated,         -   or phenoxy, which is unsubstituted or substituted by 1, 2,             3, 4 or 5 identical or different substituents selected from             the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl,             C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;     -   including their agriculturally acceptable salts     -   except for the following compounds:

-   N4-[2-(3,5-dimethylphenoxy)-6-fluoro-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine,

-   N4-[2-(3-methylphenoxy)-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine,

-   N4-[2-(3-methylphenoxy)-6-fluoro-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine,     and

-   N4-[2-(3-fluorophenoxy)-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine.     Also the following compounds

N4-(2-phenylphenyl)-1,3,5-triazine-2,4,6-triamine, known from D. Kaiser, J. of the Am. Soc, 73 1951, S. 2984,

N2-(biphenyl-4-yl)-N4,N4-dimethyl-1,3,5-triazine-2,4,6-triamine, known from WO2009/028891 and may used for preventing or treating metabolic syndrome, diabetes or cancer,

N4-[2-(4-aminophenyl)sulfonylphenyl]-1,3,5-triazine-2,4,6-triamine, known from U.S. Pat. No. 2,599,145, which may be an effective antibacterial agent,

6-(chloromethyl)-N4-(2-phenoxyphenyl)-1,3,5-triazine-2,4-diamine, known from WO 2011/140527, may be an inhibitor of p97 ATPase,

4-N-hydroxybiphenyl-butyroguanamine is known from U.S. Pat. No. 2,309,663,

N4-isopropyl-N6-phenyl-N2-(2-phenylphenyl)-1,3,5-triazine-2,4,6-triamine, N2-(2-benzylphenyl)-N4-isopropyl-N6-phenyl-1,3,5-triazine-2,4,6-triamine, N4-isopropyl-N2-(3-phenoxyphenyl)-N6-phenyl-1,3,5-triazine-2,4,6-triamine, N2-(3-benzylphenyl)-N4-isopropyl-N6-phenyl-1,3,5-triazine-2,4,6-triamine, N2-(3-benzyloxyphenyl)-N4-isopropyl-N6-phenyl-1,3,5-triazine-2,4,6-triamine, N4-isopropyl-N2-(4-phenoxyphenyl)-N6-phenyl-1,3,5-triazine-2,4,6-triamine, N2-(4-benzylphenyl)-N4-isopropyl-N6-phenyl-1,3,5-triazine-2,4,6-triamine, known from EP 1 479 397 and may used as anti dementia agents,

2-(p′-chlorophenyl-p-sulfophenyl) amino-arylamino-6-s-triazine, known from Metha, J. of the Indian Soc., 56(4), 1979, S. 383, which show therapeutic activity against several diseases, and

their agriculturally acceptable salts are not part of the present invention.

The present invention relates also to diaminotriazine compounds of formula (I)

-   -   wherein     -   p is 1 or 2;     -   q is 0, 1, 2 or 3 provided that p+q is 1, 2, 3 or 4;     -   Q is a chemical bond, O, S(O)_(m), CR^(q1)R^(q2), NR^(q3), C(O),         C(O)O, CR^(q1)R^(q2)—O, S(O)_(m)NR^(q3) or C(O)NR^(q3),         -   wherein         -   m is 0, 1 or 2;         -   R^(q1), R^(q2) are hydrogen, halogen or C₁-C₄-alkyl;         -   R^(q3) is H, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,             (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl,             (C₁-C₆-alkyl)sulfonyl, where the aliphatic parts of the 6             aforementioned radicals are unsubstituted, partly or             completely halogenated;     -   Ar is phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5         radicals R^(A) which are selected from the group consisting of         halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl,         C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl,         (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,         where the aliphatic and cycloaliphatic parts of the 22         aforementioned radicals are unsubstituted, partly or completely         halogenated and where the cycloaliphatic parts of the last 4         mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,         it being possible that R^(A) are identical or different;     -   R^(a) is selected from the group consisting of hydrogen,         halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl,         (C₁-C₆-alkyl)-carbonyloxy, where the aliphatic and         cycloaliphatic parts of the 14 aforementioned radicals are         unsubstituted, partly or completely halogenated;     -   R^(b) is selected from the group consisting of halogen, OH, CN,         amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl,         C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl,         (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,         where the aliphatic and cycloaliphatic parts of the 22         aforementioned radicals are unsubstituted, partly or completely         halogenated and where the cycloaliphatic parts of the last 4         mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,         for q=2 or 3 it being possible that R^(b) are identical or         different;     -   R¹ is selected from the group consisting of H, OH, S(O)₂NH₂, CN,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₃-C₆-cycloalkyl)-carbonyl,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl,         (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkylamino)carbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl,         di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where         the aliphatic and cycloaliphatic parts of the 15 aforementioned         radicals are unsubstituted, partly or completely halogenated,         -   phenyl, phenyl-C₁-C₆-alkyl, phenylsulfonyl,             phenylaminosulfonyl, phenylaminocarbonyl,             phenyl(C₁-C₆-alkyl)aminocarbonyl, phenylcarbonyl and             phenoxycarbonyl,         -   wherein phenyl in the last 8 mentioned radicals are             unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or             different substituents selected from the group consisting of             halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy             and C₁-C₆-haloalkoxy;     -   R² is selected from the group consisting of H, OH, S(O)₂NH₂, CN,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₃-C₆-cycloalkyl)-carbonyl         C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl,         (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl,         (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl and         (C₁-C₆-alkoxy)sulfonyl, where the aliphatic and cycloaliphatic         parts of the 15 aforementioned radicals are unsubstituted,         partly or completely halogenated,         -   phenyl, phenylsulfonyl, phenylaminosulfonyl,             phenylaminocarbonyl, phenyl(C₁-C₆-alkyl)aminocarbonyl,             phenyl-C₁-C₆ alkyl, phenoxy, phenylcarbonyl and             phenoxycarbonyl,         -   wherein phenyl in the last 9 mentioned radicals is             unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or             different substituents selected from the group consisting of             halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy             and C₁-C₆-haloalkoxy;     -   X is a radical selected from the group consisting of         -   CR³R⁴R⁵,         -   phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5             radicals R^(Ar)         -   which are identical or different;         -   NR^(3a)R^(3b),         -   OR^(3c) and         -   S(O)_(k)R^(3d) with k being 1, 2 or 3,     -   wherein     -   R³ is selected from the group consisting of H, halogen, OH, CN,         C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the aliphatic and         cycloaliphatic parts of the 9 aforementioned radicals are         unsubstituted, partly or completely halogenated;     -   R⁴ is selected from the group consisting of H, halogen, CN,         C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;     -   R⁵ is selected from the group consisting of halogen, CN,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₃-C₆-cycloalkenyl and         C₁-C₆-alkoxy-C₁-C₆-alkyl, where the aliphatic and cycloaliphatic         parts of the 7 aforementioned radicals are unsubstituted, partly         or completely halogenated;     -   R⁴ and R⁵ together with the carbon atom to which they are         attached form a moiety selected from the group consisting of         carbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, three- to         six-membered saturated or partially unsaturated heterocyclyl,         and the moiety >C═CR^(x)R^(y), where R^(x) and R^(y) are         hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;     -   R^(Ar) selected from the group consisting of halogen, OH, CN,         amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl,         C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl,         (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,         where the aliphatic and cycloaliphatic parts of the 22         aforementioned radicals are unsubstituted, partly or completely         halogenated and where the cycloaliphatic parts of the last 4         mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,     -   R^(3a), R^(3b), R^(3c) or R^(3d) are independently of one         another are selected from the group consisting of H, CN,         S(O)₂NH₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₃-C₆-cycloalkyl, (C₃-C₆-cycloalkyl)-C₁-C₆-alkyl,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)-carbonyl,         (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl,         (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl,         (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-alkylamino)sulfonyl,         di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where         the aliphatic and cycloaliphatic parts of the 15 aforementioned         radicals are unsubstituted, partly or completely halogenated,         -   phenyl, phenylsulfonyl, phenyl-C₁-C₆ alkyl,             phenylaminosulfonyl, phenylcarbonyl and phenoxycarbonyl,             wherein phenyl in the last 6 mentioned radicals is             unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or             different substituents selected from the group consisting of             halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy             and C₁-C₆-haloalkoxy, or     -   R^(3a), R^(3b) together with the nitrogen atom, to which they         are bound, form an N-bound, mono- or bicyclic heterocyclic         radical, which may have 1, 2, 3 or 4 further heteroatoms which         are selected from N, O and S, which is unsubstituted or         substituted by one or more identical or different substituents         selected from the group consisting of halogen, CN, NO₂,         C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy,         one of R^(3a), R^(3b) may also be OH, C₁-C₆-alkoxy,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy         C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,         where the aliphatic and cycloaliphatic parts of the 7         aforementioned radicals are unsubstituted, partly or completely         halogenated,         -   or phenoxy, which is unsubstituted or substituted by 1, 2,             3, 4 or 5 identical or different substituents selected from             the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl,             C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;     -   including their agriculturally acceptable salts.         The following compounds

-   N4-[2-(3,5-dimethylphenoxy)-6-fluoro-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine,

-   N4-[2-(3-methylphenoxy)-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine,

-   N4-[2-(3-methylphenoxy)-6-fluoro-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine,     and

are known from earlier filed PCT/EP2013/072055 and therefore these compounds and their agriculturally acceptable salts are not part of the present invention.

The present invention also relates to agrochemical compositions comprising at least one diaminotriazine compound of formula (I) and at least one auxiliary customary for formulating crop protection agents.

The present invention also relates to the use of diaminotriazine compound of formula (I) as herbicides, i.e. for controlling unwanted and/or harmful vegetation or plants.

The present invention furthermore provides a method for controlling unwanted plants. The method includes allowing a herbicidally effective amount of at least one diaminotriazine compound of the formula (I) to act on the unwanted plants or vegetation, their seeds and/or their habitat. Application can be done before, during and/or after, preferably during and/or after, the emergence of the unwanted plants.

Moreover, the invention relates to processes for preparing diaminotriazine compound of formula (I) and to intermediates.

Further embodiments of the present invention are evident from the claims, the description and the examples. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention.

As used herein, the terms “controlling” and “combating” are synonyms.

As used herein, the terms “undesirable vegetation”, “unwanted vegetation”, unwanted plants” and “harmful plants” are synonyms.

In the context of substituents, the term “one or more substitutents” means that the number of substituents is e.g. from 1 to 10, in particular 1, 2, 3, 4, 5, 6, 7 or 8.

If the diaminotriazine compounds of formula (I) as described herein is capable of forming geometrical isomers, for example E/Z isomers, the invention relates to both the pure isomers and mixtures thereof. Likewise, the invention relates to the use of the pure isomers and to the use of their mixtures and to compositions containing the pure isomers or mixtures thereof.

If the diaminotriazine compounds of formula (I) as described herein have one or more centres of chirality and, as a consequence, are present as enantiomers or diastereomers, the invention relates to both the pure enantiomers or diastereomers, and mixtures thereof. Likewise, the invention relates to the use of the pure enantiomers or diastereomers and to the use of the mixtures thereof and to compositions containing the pure enantiomers or diastereomers or mixtures thereof.

If the diaminotriazine compounds of formula (I) as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.

Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, (C₁-C₄-alkoxy)-C₁-C₄-alkyl, hydroxy-(C₁-C₄-alkoxy)-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethyl-ammonium (olamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)-ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogen-phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

Further embodiments of the present invention are evident from the claims, the description and the examples. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention.

The organic moieties mentioned in the definition of the variables, e.g. A, R^(A), R^(b), R^(c), R^(d), R¹, R², X, R³, R⁴, R⁵, R^(Ar), R^(3a), R^(3b), R^(3c), R^(3d), Q are—like the term halogen—collective terms for individual enumerations of the individual group members. The term halogen denotes in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, (alkyl)amino, di(alkyl)amino, alkoxyalkyl, alkoxyalkoxy, (alky)carbonyl, (alkoxy)carbonyl chains can be straight-chain or branched, the prefix C_(n)-C_(m) denoting in each case the possible number of carbon atoms in the group. The same applies to composed radicals, such as cycloalkylalkyl and phenylalkyl.

Examples of such meanings are:

C₁-C₄-alkyl and also the C₁-C₄-alkyl moieties of C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl, (C₁-C₄-alkyl)carbonyl, (C₁-C₄-alkyl)carbonyl, (C₁-C₄-alkoxy)carbonyl, (C₁-C₄-alkyl)carbonyloxy, C₁-C₄-alkyloxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, (C₁-C₄-alkylamino)carbonyl, di(C₁-C₄-alkyl)aminocarbonyl, (C₁-C₄-alkylamino)sulfonyl, di(C₁-C₄-alkyl)aminosulfonyl or phenyl-C₁-C₄-alkyl: for example CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, CH(CH₃)—C₂H₅, CH₂—CH(CH₃)₂ and C(CH₃)₃;

C₁-C₆-alkyl and also the C₁-C₆-alkyl moieties of C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)carbonyloxy, C₁-C₆-alkyloxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, phenyl(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl or phenyl-C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above, and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl;

C₂-C₆-alkenyl and also the C₂-C₆-alkenyl moieties of (C₁-C₆-alkoxy)-C₂-C₆-alkenyl: a linear or branched ethylenically unsaturated hydrocarbon group having 2 to 6 carbon atoms and a C═C-double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

C₂-C₆-alkynyl and also the C₂-C₆-alkynyl moieties of (C₁-C₆-alkoxy)-C₂-C₆-alkynyl: linear or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing at least one C—C-triple bond, such as ethynyl, 1-propynyl, 2-propynyl (propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1,1,2,2,-tetrafluoroethyl and 1-trifluoromethyl-1,2,2,2-tetrafluoroethyl;

C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;

C₃-C₆-cycloalkyl: monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

C₁-C₆-alkoxy and also the C₁-C₆-alkoxy moieties of (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkoxy)sulfonyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl: C₁-C₄-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloro-methoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloro-propoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 4-fluorobutoxy, nonafluorobutoxy, 1,1,2,2,-tetrafluoroethoxy and 1-trifluoromethyl-1,2,2,2-tetrafluoroethoxy;

C₁-C₆-haloalkoxy: C₁-C₄-alkoxy as mentioned above: C₁-C₄-haloalkoxy as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;

C₂-C₆-alkenyloxy: C₂-C₆-alkenyl as defined above, which is bound via an oxygen atom, such as ethenyloxy (vinyloxy), 1-propenyloxy, 2-propenyloxy (allyloxy), 1-butenyloxy, 2-butenyloxy, 3-butenyloxy 1-methyl-2-propenyloxy and the like;

C₂-C₆-alkynyloxy: C₂-C₆-alkynyl as defined above, which is bound via an oxygen atom, such as ethynyloxy, 1-propynyl, 2-propynyloxy (propargyloxy), 1-butynyloxy, 2-butynyloxy, 3-butynyloxy 1-methyl-2-propynyloxy and the like;

C₁-C₄-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;

C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;

C₁-C₆-alkylsulfinyl (C₁-C₆-alkyl-S(═O)—): z.B. methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutyl-sulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutyl-sulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl;

C₁-C₆-alkylsulfonyl (C₁-C₆-alkyl-S(O)₂—): for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

(C₁-C₄-alkyl)amino and also the (C₁-C₄-alkylamino) moieties of (C₁-C₄-alkylamino)carbonyl or (C₁-C₄-alkylamino)sulfonyl: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino or 1,1-dimethylethylamino;

(C₁-C₆-alkyl)amino and also the (C₁-C₆-alkylamino) moieties of (C₁-C₆-alkylamino)carbonyl, phenyl(C₁-C₆-alkyl)aminocarbonyl or (C₁-C₆-alkylamino)sulfonyl: (C₁-C₄-alkyl)amino as mentioned above, and also, for example, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutyl-amino 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;

di(C₁-C₄-alkyl)amino and also the di(C₁-C₄-alkylamino) moieties of di(C₁-C₄-alkylamino)carbonyl or di(C₁-C₄-alkylamino)sulfonyl: for example N,N-dimethylamino, N,N-diethylamino, N,N-di(1-methylethyl)amino, N,N-dipropylamino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethyl-ethyl)-N-(2-methylpropyl)amino;

di(C₁-C₆-alkyl)amino and also the di(C₁-C₆-alkylamino) moieties of di(C₁-C₆-alkylamino)carbonyl or di(C₁-C₆-alkylamino)sulfonyl: di(C₁-C₄-alkyl)amino as mentioned above, and also, for example, N-methyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-methyl-N-(3-methyl-butyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1-ethylpropyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1,1-dimethylpropyl)amino, N-methyl-N-(1,2-dimethylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylpentyl)amino, N-methyl-N-(3-methylpentyl)amino, N-methyl-N-(4-methylpentyl)amino, N-methyl-N-(1,1-dimethylbutyl)amino, N-methyl-N-(1,2-dimethylbutyl)amino, N-methyl-N-(1,3-dimethylbutyl)amino, N-methyl-N-(2,2-dimethylbutyl)amino, N-methyl-N-(2,3-dimethylbutyl)amino, N-methyl-N-(3,3-dimethylbutyl)amino, N-methyl-N-(1-ethylbutyl)amino, N-methyl-N-(2-ethylbutyl)amino, N-methyl-N-(1,1,2-trimethylpropyl)amino, N-methyl-N-(1,2,2-trimethylpropyl)amino, N-methyl-N-(1-ethyl-1-methylpropyl)amino, N-methyl-N-(1-ethyl-2-methylpropyl)amino, N-ethyl-N-pentylamino, N-ethyl-N-(1-methylbutyl)amino, N-ethyl-N-(2-methylbutyl)amino, N-ethyl-N-(3-methylbutyl)amino, N-ethyl-N-(2,2-dimethylpropyl)amino, N-ethyl-N-(1-ethylpropyl)amino, N-ethyl-N-hexylamino, N-ethyl-N-(1,1-dimethylpropyl)amino, N-ethyl-N-(1,2-dimethylpropyl)amino, N-ethyl-N-(1-methylpentyl)amino, N-ethyl-N-(2-methylpentyl)amino, N-ethyl-N-(3-methylpentyl)amino, N-ethyl-N-(4-methylpentyl)amino, N-ethyl-N-(1,1-dimethylbutyl)amino, N-ethyl-N-(1,2-dimethylbutyl)amino, N-ethyl-N-(1,3-dimethylbutyl)amino, N-ethyl-N-(2,2-dimethylbutyl)amino, N-ethyl-N-(2,3-dimethylbutyl)amino, N-ethyl-N-(3,3-dimethylbutyl)amino, N-ethyl-N-(1-ethylbutyl)-amino, N-ethyl-N-(2-ethylbutyl)amino, N-ethyl-N-(1,1,2-trimethylpropyl)amino, N-ethyl-N-(1,2,2-trimethylpropyl)amino, N-ethyl-N-(1-ethyl-1-methylpropyl)amino, N-ethyl-N-(1-ethyl-2-methylpropyl)amino, N-propyl-N-pentylamino, N-butyl-N-pentylamino, N,N-di-pentylamino, N-propyl-N-hexylamino, N-butyl-N-hexylamino, N-pentyl-N-hexylamino or N,N-dihexylamino;

C₃-C₆-cyclolalkyl and also the C₃-C₆-cyclolalkyl moieties of (C₃-C₆-cyclolalkyl)-carbonyl, (C₃-C₆-cyclolalkyl)-C₁-C₆-alkyl, (C₃-C₆-cycloalkyl)carbonyl and (C₃-C₆-cyclolalkyl)-C₁-C₆-alkoxy: a cycloaliphatic radical having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C₃-C₆-cyclolalkoxy: a cycloaliphatic radical having 3 to 6 carbon atoms and bound via an oxygen atom, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy and cyclohexyloxy;

(C₃-C₆-cyclolalkyl)-C₁-C₆-alkyl: C₁-C₆-alkyl, in particular C₁-C₄-alkyl as defined above, such as methyl or ethyl, wherein 1 hydrogen atom is replaced by C₃-C₆-cyclolalkyl as defined above, examples including cyclopropylmethyl (CH₂-cyclopropyl), cyclobutylmethyl, cyclopentylmethyl, cycloexylmethyl, 1-cyclopropylethyl (CH(CH₃)-cyclopropyl), 1-cyclobutylethyl, 1-cyclopentylethyl, 1-cycloexylethyl, 2-cyclopropylethyl (CH₂CH₂-cyclopropyl), 2-cyclobutylethyl, 2-cyclopentylethyl or 2-cycloexylethyl;

(C₃-C₆-cyclolalkyl)-C₁-C₆-alkoxy: C₁-C₆-alkoxy, in particular C₁-C₄-alkoxy as defined above, such as methoxy or ethoxy, wherein 1 hydrogen atom is replaced by C₃-C₆-cyclolalkyl as defined above, examples including cyclopropylmethoxy (OCH₂-cyclopropyl), cyclobutylmethoxy, cyclopentylmethoxy, cycloexylmethoxy, 1-cyclopropylethoxy (O—CH(CH₃)-cyclopropyl), 1-cyclobutylethoxy, 1-cyclopentylethoxy, 1-cycloexylethoxy, 2-cyclopropylethoxy (OCH₂CH₂)-cyclopropyl), 2-cyclobutylethoxy, 2-cyclopentylethoxy and 2-cycloexylethoxy;

(C₁-C₆-alkoxy)-C₁-C₆-alkyl: C₁-C₆-alkyl, in particular C₁-C₄-alkyl as defined above, such as methyl, ethyl or isopropyl, wherein 1 hydrogen atom is replaced by C₁-C₆-alkoxy as defined above, examples including methoxymethyl, ethoxymethyl, n-propoxymethyl, butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-(n-propoxy)ethyl, 1-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-(n-propoxy)ethyl, 2-butoxyethyl, 2-methoxypropyl, 2-ethoxypropyl, 2-(n-propoxy)propyl, 2-butoxypropyl;

(C₁-C₆-alkoxy)-C₁-C₆-alkoxy: C₁-C₆-alkoxy, in particular C₁-C₄-alkoxy as defined above, such as methoxy or ethoxy, wherein 1 hydrogen atom is replaced by C₁-C₆-alkoxy as defined above, examples including methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, butoxymethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-(n-propoxy)ethoxy and 2-butoxyethoxy;

(C₁-C₆-alkoxy)-C₂-C₆-alkenyl: C₂-C₆-alkenyl, in particular C₂-C₄-alkenyl as defined above, such as ethenyl, propenyl, 1-butenyl or 2-butenyl, wherein 1 hydrogen atom is replaced by C₁-C₆-alkoxy as defined above;

(C₁-C₆-alkoxy)-C₂-C₆-alkynyl: C₂-C₆-alkynyl, in particular C₂-C₄-alkynyl as defined above, such as ethynyl, propynyl or 2-butynyl, wherein 1 hydrogen atom is replaced by C₁-C₆-alkoxy as defined above;

(C₁-C₆-alkyl)carbonyl: C₁-C₆-alkyl as mentioned above, which is bound to the remainder of the molecule by a carbonyl group;

(C₁-C₆-alkoxy)carbonyl: C₁-C₆-alkyloxy as mentioned above, which is bound to the remainder of the molecule by a carbonyl group;

(C₁-C₆-alkylamino)carbonyl: (C₁-C₆-alkyl)amino as mentioned above, which is bound to the remainder of the molecule by a carbonyl group;

(C₁-C₆-alkylamino)sulfonyl: (C₁-C₆-alkyl)amino as mentioned above, which is bound to the remainder of the molecule by a sulfonyl group;

di(C₁-C₆-alkylamino)carbonyl: di(C₁-C₆-alkyl)amino as mentioned above, which is bound to the remainder of the molecule by a carbonyl group;

di(C₁-C₆-alkylamino)sulfonyl: di(C₁-C₆-alkyl)amino as mentioned above, which is bound to the remainder of the molecule by a sulfonyl group;

phenyl-C₁-C₆-alkyl: C₁-C₆-alkyl, in particular C₁-C₄-alkyl as defined above, such as methyl or ethyl, wherein 1 hydrogen atom is replaced by phenyl, examples including benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 1-phenyl-1-methylethyl etc.;

three- to six-membered heterocyclyl: monocyclic saturated or partially unsaturated hydrocarbon having three to six ring members as mentioned above which, in addition to carbon atoms, contains one or two heteroatoms selected from O, S and N;

for example

saturated heterocycles such as 2-oxiranyl, 2-oxetanyl, 3-oxetanyl, 2-aziridinyl, 3-thietanyl, 1-azetidinyl, 2-azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,4-dithian-2-yl, 1,3-dithian-5-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydro-thiopyranyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-6-yl, 2-morpholinyl, 3-morpholinyl or 4-morpholinyl, for example 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl;

partially unsaturated heterocycles such as 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 4,5-dihydropyrrol-2-yl, 4,5-dihydropyrrol-3-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 4,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-3-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 2,3-dihydrothiazol-3-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl, 3,4-dihydrothiazol-5-yl, 3,4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl, 3,6-dihydro-2H-pyran-2-yl, 3,6-dihydro-2H-pyran-3-yl, 3,6-dihydro-2H-pyran-4-yl, 3,6-dihydro-2H-pyran-5-yl, 3,6-dihydro-2H-pyran-6-yl, 3,4-dihydro-2H-pyran-3-yl, 3,4-dihydro-2H-pyran-4-yl, 3,4-dihydro-2H-pyran-6-yl, 5,6-dihydro-4H-1,3-oxazin-2-yl;

5- and 6-membered hetaryl which contains 1, 2 or 3 heteroatoms selected from O, S and N:

5-membered or 6-membered heteroaromatic radical, which besides carbon atoms contains 1, 2 or 3 heteroatoms as ring members, which are selected from O, S and N e.g. 1, 2 or 3 nitrogen atoms or 1 oxygen or sulfur atom and optionally 1 or 2 nitrogen atoms:

in particular:

five-membered monocyclic heteroaryl which contains one to three heteroatoms selected from O, S and N:

for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl etc.;

six-membered monocyclic heteroaryl contains one to three nitrogen atoms as ring members:

for example 2-pyridinyl (2-pyridyl), 3-pyridinyl (3-pyridyl), 4-pyridinyl (4-pyridyl), 1-oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl and 1,2,3-triazinyl, 1,2,4-triazinyl and 1,3,5-triazinyl.

The preferred embodiments of the invention mentioned herein below have to be understood as being preferred either independently from each other or in combination with one another. Particular groups of embodiments of the invention relate to those diaminotriazines of formula (I), wherein the variables R¹, R², R^(a), R^(b), Ar, R^(A), X, q and p either independently of one another or in combination with one another, have the following meanings:

Particular groups of embodiments relate to the diaminotriazine compounds of formula (I), wherein

-   Ar is phenyl, which is substituted by 1, 2 or 3 substituents R^(A),     wherein R^(A) is as defined above and in particular R^(A) is     selected from the group consisting of halogen, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy; particularly     preferred selected from the group consisting of halogen,     C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;     -   especially preferred selected from halogen, C₁-C₄-alkyl and CN;     -   also especially preferred selected from the group consisting of         F, Cl, CN and CH₃;     -   more preferred selected from the group consisting of F, Cl and         CN. -   Ar is particularly preferred phenyl, which is substituted by 1 or 2     substituents R^(A), which is as defined above, particularly R^(A) is     selected from the group consisting of halogen, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy; particularly     preferred selected from the group consisting of halogen,     C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;     -   especially preferred selected from halogen, C₁-C₄-alkyl and CN;     -   also especially preferred selected from the group consisting of         F, Cl, CN and CH₃;     -   more preferred selected from the group consisting of F, Cl and         CN. -   Ar is also specially preferred phenyl, which is substituted by 1     substituents R^(A), which is as defined above, particularly R^(A) is     selected from the group consisting of halogen, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy;     -   particularly preferred selected from the group consisting of         halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,         C₁-C₄-haloalkoxy;     -   especially preferred selected from halogen, C₁-C₄-alkyl and CN;     -   also especially preferred selected from the group consisting of         F, Cl, CN and CH₃;     -   more preferred selected from the group consisting of F, Cl and         CN. -   Ar is also especially preferred phenyl, which is substituted by 2     substituents R^(A), which is as defined above, particularly R^(A) is     selected from the group consisting of halogen, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy;     -   particularly preferred selected from the group consisting of         halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,         C₁-C₄-haloalkoxy;     -   especially preferred selected from halogen, C₁-C₄-alkyl and CN;     -   also especially preferred selected from the group consisting of         F, Cl, CN and CH₃;     -   more preferred selected from the group consisting of F, Cl and         CN.

Likewise particular groups of embodiments relate to the diaminotriazine compounds of formula (I), wherein

-   Ar is phenyl, which is substituted by 1, 2 or 3 substituents R^(A),     wherein R^(A) is as defined above and in particular R^(A) is     selected from the group consisting of halogen, CN, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy,     C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,     (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkyl)amino,     di(C₁-C₆-alkyl)amino, (C₁-C₆-alkyl)-carbonyl,     (C₁-C₆-alkoxy)-carbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,     (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,     where the aliphatic and cycloaliphatic parts of the 12     aforementioned radicals are unsubstituted, partly or completely     halogenated and where the cycloaliphatic parts of the last 4     mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,     -   phenyl, phenyl-C₁-C₄-alkyl, wherein phenyl in the last 2         mentioned radicals are unsubstituted or substituted by 1, 2, 3,         4 or 5 identical or different substituents selected from the         group consisting of halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;     -   particularly preferred selected from the group consisting of         halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,         C₁-C₄-haloalkoxy, C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy,         (C₁-C₄-alkoxy)-C₁-C₄-alkyl, (C₁-C₄-alkoxy)-C₁-C₄-alkoxy,         di(C₁-C₆-alkyl)amino, (C₁-C₄-alkoxy)-carbonyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the         aliphatic and cycloaliphatic parts of the 9 aforementioned         radicals are unsubstituted, partly or completely halogenated,         phenyl, wherein phenyl is unsubstituted or substituted by 1, 2,         3, 4 or 5 identical or different substituents selected from the         group consisting of halogen, CN, C₁-C₄-alkyl;     -   especially preferred selected from halogen, CN, C₁-C₄-alkyl,         C₁-C₄-haloalkyl, CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,         C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy, (C₁-C₄-alkoxy)-C₁-C₄-alkoxy,         di(C₁-C₆-alkyl)amino, (C₁-C₄-alkoxy)-carbonyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy and phenyl;         also especially preferred selected from the group consisting of         F, Cl, I, CN, CF₃, CH(CH₃)₂, CH₂CH₃, methoxycarbonyl, C(CH₃)₃,         Br, I, OCHF₂, OCF₃, OCH(CH₃)₂, OCH₂CH₃, prop-2-ynoxy,         OCH₂CH₂—OCH₂CH₃, allyloxy, phenyl, isobutoxy, OCH₂CHF₂, OCH₂CF₃,         cyclobutylmethoxy, cyclopentoxy, cyclohexoxy and CH₃; more         preferred selected from the group consisting of F, Cl, CF₃ and         CN. -   Ar is particularly preferred phenyl, which is substituted by 1 or 2     substituents R^(A), which is as defined above, particularly R^(A) is     selected from the group consisting of halogen, CN, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy,     C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,     (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkyl)amino,     di(C₁-C₆-alkyl)amino, (C₁-C₆-alkyl)-carbonyl,     (C₁-C₆-alkoxy)-carbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,     (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,     where the aliphatic and cycloaliphatic parts of the 12     aforementioned radicals are unsubstituted, partly or completely     halogenated and where the cycloaliphatic parts of the last 4     mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,     -   phenyl, phenyl-C₁-C₄-alkyl, wherein phenyl in the last 2         mentioned radicals are unsubstituted or substituted by 1, 2, 3,         4 or 5 identical or different substituents selected from the         group consisting of halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;     -   particularly preferred selected from the group consisting of         halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,         C₁-C₄-haloalkoxy, C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy,         (C₁-C₄-alkoxy)-C₁-C₄-alkyl, (C₁-C₄-alkoxy)-C₁-C₄-alkoxy,         di(C₁-C₆-alkyl)amino, (C₁-C₄-alkoxy)-carbonyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the         aliphatic and cycloaliphatic parts of the 9 aforementioned         radicals are unsubstituted, partly or completely halogenated,         phenyl, wherein phenyl is unsubstituted or substituted by 1, 2,         3, 4 or 5 identical or different substituents selected from the         group consisting of halogen, CN, C₁-C₄-alkyl;     -   especially preferred selected from halogen, C₁-C₄-alkyl, CN,         C₁-C₄-haloalkyl, CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,         C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy, (C₁-C₄-alkoxy)-C₁-C₄-alkoxy,         di(C₁-C₆-alkyl)amino, (C₁-C₄-alkoxy)-carbonyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy and phenyl;         also especially preferred selected from the group consisting of         F, Cl, I, CN, CF₃, CH(CH₃)₂, CH₂CH₃, methoxycarbonyl, C(CH₃)₃,         Br, I, OCHF₂, OCF₃, OCH(CH₃)₂, OCH₂CH₃, prop-2-ynoxy,         OCH₂CH₂—OCH₂CH₃, allyloxy, phenyl isobutoxy, OCH₂CHF₂, OCH₂CF₃,         cyclobutylmethoxy, cyclopentoxy, cyclohexoxy and CH₃;     -   more preferred selected from the group consisting of F, Cl, CF₃         and CN. -   Ar is also specially preferred phenyl, which is substituted by 1     substituents R^(A), which is as defined above, particularly R^(A) is     selected from the group consisting of halogen, CN, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy,     C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)amino,     di(C₁-C₆-alkyl)amino, (C₁-C₆-alkyl)-carbonyl,     (C₁-C₆-alkoxy)-carbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,     (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,     where the aliphatic and cycloaliphatic parts of the 11     aforementioned radicals are unsubstituted, partly or completely     halogenated and where the cycloaliphatic parts of the last 4     mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups;     -   phenyl, phenyl-C₁-C₄-alkyl, wherein phenyl in the last 2         mentioned radicals are unsubstituted or substituted by 1, 2, 3,         4 or 5 identical or different substituents selected from the         group consisting of halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;     -   particularly preferred selected from the group consisting of         halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,         C₁-C₄-haloalkoxy, C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy,         (C₁-C₄-alkoxy)-C₁-C₄-alkyl, (C₁-C₄-alkoxy)-C₁-C₄-alkoxy,         di(C₁-C₆-alkyl)amino, (C₁-C₄-alkoxy)-carbonyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the         aliphatic and cycloaliphatic parts of the 9 aforementioned         radicals are unsubstituted, partly or completely halogenated,         phenyl, wherein phenyl is unsubstituted or substituted by 1, 2,         3, 4 or 5 identical or different substituents selected from the         group consisting of halogen, CN, C₁-C₄-alkyl;     -   especially preferred selected from halogen, C₁-C₄-alkyl, CN,         C₁-C₄-haloalkyl, CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,         C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy, (C₁-C₄-alkoxy)-C₁-C₄-alkoxy,         di(C₁-C₆-alkyl)amino, (C₁-C₄-alkoxy)-carbonyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy and phenyl;         also especially preferred selected from the group consisting of         F, Cl, I, CN, CF₃, CH(CH₃)₂, CH₂CH₃, methoxycarbonyl, C(CH₃)₃,         Br, I, OCHF₂, OCF₃, OCH(CH₃)₂, OCH₂CH₃, prop-2-ynoxy,         OCH₂CH₂—OCH₂CH₃, allyloxy, phenyl, isobutoxy, OCH₂CHF₂, OCH₂CF₃,         cyclobutylmethoxy, cyclopentoxy, cyclohexoxy and CH₃;     -   more preferred selected from the group consisting of F, Cl, CF₃         and CN. -   Ar is also especially preferred phenyl, which is substituted by 2     substituents R^(A), which is as defined above, particularly R^(A) is     selected from the group consisting of halogen, CN, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy,     C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)amino,     di(C₁-C₆-alkyl)amino, (C₁-C₆-alkyl)-carbonyl,     (C₁-C₆-alkoxy)-carbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,     (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy,     where the aliphatic and cycloaliphatic parts of the 11     aforementioned radicals are unsubstituted, partly or completely     halogenated and where the cycloaliphatic parts of the last 4     mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups;     -   phenyl, phenyl-C₁-C₄-alkyl, wherein phenyl in the last 2         mentioned radicals are unsubstituted or substituted by 1, 2, 3,         4 or 5 identical or different substituents selected from the         group consisting of halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;         -   particularly preferred selected from the group consisting of             halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,             C₁-C₄-haloalkoxy, C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy,             (C₁-C₄-alkoxy)-C₁-C₄-alkyl, (C₁-C₄-alkoxy)-C₁-C₄-alkoxy,             di(C₁-C₆-alkyl)amino, (C₁-C₄-alkoxy)-carbonyl,             C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,             (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the aliphatic and             cycloaliphatic parts of the 9 aforementioned radicals are             unsubstituted, partly or completely halogenated, phenyl,             wherein phenyl is unsubstituted or substituted by 1, 2, 3, 4             or 5 identical or different substituents selected from the             group consisting of halogen, CN, C₁-C₄-alkyl;     -   especially preferred selected from halogen, C₁-C₄-alkyl, CN,         C₁-C₄-haloalkyl, CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,         C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy, (C₁-C₄-alkoxy)-C₁-C₄-alkoxy,         di(C₁-C₆-alkyl)amino, (C₁-C₄-alkoxy)-carbonyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy and phenyl;     -   also especially preferred selected from the group consisting of         F, Cl, I, CN, CF₃, CH(CH₃)₂, CH₂CH₃, methoxycarbonyl, C(CH₃)₃,         Br, I, OCHF₂, OCF₃, OCH(CH₃)₂, OCH₂CH₃, prop-2-ynoxy,         OCH₂CH₂—OCH₂CH₃, allyloxy, phenyl, isobutoxy, OCH₂CHF₂, OCH₂CF₃,         cyclobutylmethoxy, cyclopentoxy, cyclohexoxy and CH₃;     -   more preferred selected from the group consisting of F, Cl, CF₃         and CN.         In this context Q has the meaning as defined above.         In particular -   Q is a chemical bond, O, CR^(q1)R^(q2), S, S(O) or S(O)₂, wherein     R^(q1) and R^(q2) are identical or different selected from the group     of hydrogen, halogen, such as F or Cl or C₁-C₄-alkyl, such as CH₃;     more particular selected from the group, hydrogen or C₁-C₄-alkyl,     Especially preferred     Q is a chemical bond, O, CH₂, S, S(O) or S(O)₂.     Likewise in particular -   Q is NR^(q3), wherein R^(q3) is selected from H, CN and C₁-C₆-alkyl,     -   more particular R^(q3) is selected from H, CN C₁-C₄-alkyl, such         as CH₃; selected from the group, hydrogen or C₁-C₄-alkyl,         Especially preferred R^(q3) is selected from H or CH₃.         A preferred embodiment relate to the diaminotriazine compound of         formula (I), wherein wherein the moiety

is represented by one of the following moieties A or B

wherein

-   Ar, Q, R^(a) are as defined above and wherein R^(b1), R^(b2) and     R^(b3) are identical or different and are hydrogen or have one of     the meanings of R^(b), wherein -   R^(b) is selected from the group consisting of halogen, CN,     C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,     C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, where the aliphatic parts of the     6 aforementioned radicals are unsubstituted, partly or completely     halogenated and     for q=2 or 3 it being possible that R^(b) are identical or     different.     More particular -   R^(b) is selected halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,     C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,     C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy, for q=2 or 3 it being possible     that R^(b) are identical or different.     Even more particular -   R^(b) is selected F, Cl, Br, methyl. -   R^(a) is selected from the group consisting of halogen, CN,     C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,     C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, where the aliphatic parts of the     6 aforementioned radicals are unsubstituted, partly or completely     halogenated and     for q=2 or 3 it being possible that R^(b) _([FVD1]) are identical or     different.     More particular -   R^(a) is selected halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,     C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,     C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy.     Even more particular -   R^(a) is selected F, Cl, Br, CN, methyl.     More particular Q, A, R^(b) and R^(a) has the meanings as defined     above and     R^(b1) is selected from the group consisting of and hydrogen and     fluorine;     R^(b2) is selected from the group consisting of and hydrogen and     fluorine;     R^(b3) is selected from the group consisting of and hydrogen and     fluorine.

Especially preferred examples of the moiety Ar-Q is selected from the group consisting of phenyl, 4-methoxyphenyl, 4-cyanophenyl, 3-methylphenyl, 3,5-dimethylphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,5-dibromophenyl, 3,5-dimethoxyphenyl, 3,5-diethoxyphenyl, 3,5-Bis-(trifluoromethoxy)phenyl, 3,5-Bis-(trifluoromethyl)phenyl, 3,5-dicyanophenyl, 3-fluoro-5-methylphenyl, 3-chloro-5-methylphenyl, 3-bromo-5-methylphenyl, 3-methoxy-5-methylphenyl, 3-ethoxy-5-methylphenyl, 3-(trifluoromethoxy)-5-methylphenyl, 3-(trifluoromethyl)-5-methylphenyl, 3-(tert.-butyl)-5-methylphenyl, 3-cyano-5-methylphenyl, 3-chloro-5-fluorophenyl, 3-bromo-5-fluorophenyl, 3-fluoro-5-methoxyphenyl, 3-fluoro-5-ethoxyphenyl, 3-fluoro-5-(trifluoromethoxy)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 3-fluoro-5-(tert-butyl)phenyl, 3-fluoro-5-cyanophenyl, 3-chloro-5-methoxyphenyl, 3-chloro-5-ethoxyphenyl, 3-chloro-5-(trifluoromethoxy)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-chloro-5-(tert-butyl)phenyl, 3-chloro-5-cyanophenyl, 3-bromo-5-methoxyphenyl, 3-bromo-5-ethoxyphenyl, 3-bromo-5-(trifluoromethoxy)phenyl, 3-bromo-5-(trifluoromethyl)phenyl, 3-bromo-5-(tert-butyl)phenyl, 3-bromo-5-cyanophenyl, 3-ethoxy-5-methoxyphenyl, 3-(trifluoromethoxy)-5-methoxyphenyl, 3-methoxy-5-(trifluoromethyl)phenyl, 5-cyano-3-methoxyphenyl, 5-(tert-butyl)-3-methoxyphenyl, 3-(trifluoromethoxy)-5-ethoxyphenyl, 3-ethoxy-5-(trifluoromethyl)phenyl, 5-cyano-3-ethoxyphenyl, 5-(tert-butyl)-3-ethoxyphenyl, 3-(trifluoromethoxy)-5-(trifluoromethyl)phenyl, 3-(trifluoromethoxy)-5-(tert.-butyl)phenyl, 3-(trifluoromethoxy)-5-cyanophenyl, 3-(trifluoromethyl)-5-(tert.-butyl)phenyl, 3-(trifluoromethyl)-5-cyanophenyl, 3-cyano-5-(tert.-butyl)phenyl and 3,5-bis(tert.-butyl)phenyl.

Likewise especially preferred examples of the moiety Ar-Q is selected from the group consisting of 3,5-bis(trifluoromethyl)phenoxy, 3-fluoro-5-(trifluoromethyl)phenoxy, 3-chloro-5-fluoro-phenoxy, 3,5-bis(bromo)phenoxy, 3-bromo-5-fluoro-phenoxy, 3-chloro-5-(methoxy)phenoxy, 3-chloro-5-bromo-phenoxy, 3-fluoro-5-cyano-phenoxy, 3-bromo-5-trifluormethoxy-phenoxy, 3-bromo-5-methoxy-phenoxy, 3-fluoro-5-methoxy-phenoxy, 3-methyl-5-methoxy-phenoxy, 3-chloro-5-trifluormethoxy-phenoxy, 3-trifluormethoxy-5-trifluomethyl-phenoxy, 3-methyl-5-trifluormethyl-phenoxy, 3-iodo-5-iodo-phenoxy, 3-ethoxy-5-ethoxy-phenoxy, 3-methyl-5-propoxy-phenoxy, 3-bromo-5-isopropoxy-phenoxy, 3-methyl-5-ethoxy-phenoxy, 3-methyl-5-(prop-2-ynoxy)-phenoxy, 3-bromo-5-trifluormethyl-phenoxy, 3-chloro-5-trifluormethyl-phenoxy, 3-methyl-5-(2-ethoxyethoxy)-phenoxy, 3-methyl-5-allyloxy-phenoxy, 3-methyl-5-methyl-phenoxy, 3-methyl-5-isobutoxy-phenoxy, 3-methyl-5-(2,2-difluoroethoxy)-phenoxy, 3-methyl-5-dimethylamino-phenoxy, 3-methyl-5-(2,2,2-trifluoroethoxy)-phenoxy, 3-fluoro-5-difluoromethoxy-phenoxy, 3-methyl-5-(cyclobutylmethoxy)-phenoxy, 3-iodo-5-methoxy-phenoxy, 3-methyl-5-cyclopentoxy-phenoxy, 3-methyl-5-cyclohexoxy-phenoxy, 3-trifluoromethyl-5-phenyl-phenoxy, 3-trifluoromethyl-phenoxy, 3-isopropoxy-phenoxy, 3-ethyl-phenoxy, 3-methoxycarbonyl-phenoxy, 3-tert-butyl-phenoxy, 3-bromo-phenoxy, 3-chloro-phenoxy, 3-difluoromethoxy-phenoxy, 3-iodo-5-methoxy-phenoxy, 3-trifluormethoxy-phenoxy, 3-difluoromethoxy-5-phenyl-phenoxy, 3-isopropoxy-5-fluoro-phenoxy, 3-iodo-5-fluoro-phenoxy, N-methyl-N-phenyl-amine and N-methyl-N-(m-tolyl)-amine, 3-methyl-phenoxy, 3-fluoro-phenoxy, 3-chloro-5-chloro-phenoxy, 3,5-dimethyl-4-chloro-phenoxy, 3,4-dimethyl-phenoxy, 2,4-dimethyl-phenoxy, 2-methyl-phenoxy, 3-flouro-5-fluoro-phenoxy, phenoxy, 2,3-dimethyl-phenoxy, 3,5-diethoxy-phenoxy, 3-methyl-5-chloro-phenoxy, 2,5-dimethyl-phenoxy, 2,6-dimethyl-phenoxy, 3-methoxy-phenyl, 4-methyl-phenyl, 4-methoxy-phenyl, 4-chloro-phenyl, 4-cyano-phenyl.

Further particular groups of embodiment relate to the diaminotriazine compound of formula (I), wherein R^(a) is defined above.

In particular

-   R^(a) is selected from the group consisting of halogen, CN,     C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,     C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, where the aliphatic parts of the     6 aforementioned radicals are unsubstituted, partly or completely     halogenated and     More particular -   R^(a) is selected halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,     C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,     C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy.     Even more particular -   R^(a) is selected F, Cl, Br, CN, methyl.

Further particular groups of embodiment relate to the diaminotriazine compound of formula (I), wherein R^(b) is defined above.

In particular

-   R^(b) is selected from the group consisting of halogen, CN,     C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,     C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, where the aliphatic parts of the     6 aforementioned radicals are unsubstituted, partly or completely     halogenated and     -   for q=2 or 3 it being possible that R^(b) are identical or         different.         More particular -   R^(b) is selected halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,     C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,     C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy.     Even more particular -   R^(b) is selected F, Cl, Br, CN, methyl.

Further particular groups of embodiment relate to the diaminotriazine compound of formula (I), wherein:

-   R¹ is H, OH, S(O)₂NH₂, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl,     C₂-C₆-alkynyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₁-C₆-alkoxy,     (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)-carbonyl,     (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl,     (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkylamino)carbonyl,     di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl,     di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where the     aliphatic and cycloaliphatic parts of the 15 aforementioned radicals     are unsubstituted, partly or completely halogenated,     -   phenyl, phenyl-C₁-C₆-alkyl, phenylsulfonyl, phenylaminosulfonyl,         phenylcarbonyl and phenoxycarbonyl,     -   wherein phenyl in the last 6 mentioned radicals are         unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or         different substituents selected from the group consisting of         halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and         C₁-C₆-haloalkoxy;     -   preferably, H, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,         (C₁-C₆-alkyl)carbonyl (C₃-C₆-cycloalkyl)-carbonyl or         (C₁-C₆-alkyl)sulfonyl, where the aliphatic parts of the 5         aforementioned radicals unsubstituted partly or completely         halogenated, phenyl and phenyl-C₁-C₆ alkyl,     -   wherein phenyl in the last 2 mentioned radical is unsubstituted         or substituted by 1, 2, 3, 4, or 5 identical or different         substituents selected from the group consisting of halogen, CN,         NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and         C₁-C₆-haloalkoxy;     -   in particular H, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl, C₁-C₆-alkoxy, (C₁-C₆-alkyl)carbonyl,         (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-haloalkyl)carbonyl,         (C₁-C₆-alkyl)sulfonyl or (C₁-C₆-haloalkyl)sulfonyl;     -   more particularly H, CN, C₁-C₄-alkyl,         (C₁-C₄-alkoxy)-C₁-C₄-alkyl, C₁-C₄-alkoxy, (C₁-C₄-alkyl)carbonyl,         (C₃-C₆-cycloalkyl)-carbonyl, or (C₁-C₄-alkyl)sulfonyl; even more         particularly H, CN, CH₃, CH₂OCH₃, OCH₃, C(O)CH₃, C(O)cyclopropyl         or SO₂CH₃;     -   especially hydrogen.

Further particular groups of embodiments relate to the diaminotriazine compounds of formula (I), wherein;

-   R² is H, OH, S(O)₂NH₂, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl,     C₂-C₆-alkynyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₁-C₆-alkoxy,     (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl,     (C₁-C₆-alkoxy)carbonyl, (C₃-C₆-cycloalkyl)-carbonyl,     (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkylamino)carbonyl,     di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl,     di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where the     aliphatic and cycloaliphatic parts of the 15 aforementioned radicals     are unsubstituted, partly or completely halogenated,     -   phenyl, phenylsulfonyl, phenylaminosulfonyl, phenyl-C₁-C₆ alkyl,         phenoxy, phenylcarbonyl and phenoxycarbonyl,     -   wherein phenyl in the last 6 mentioned radicals is unsubstituted         or substituted by 1, 2, 3, 4 or 5 identical or different         substituents selected from the group consisting of halogen, CN,         NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and         C₁-C₆-haloalkoxy;     -   preferably, H, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,         (C₁-C₆-alkyl)carbonyl, (C₃-C₆-cycloalkyl)-carbonyl or         (C₁-C₆-alkyl)sulfonyl, where the aliphatic parts of the 4         aforementioned radicals unsubstituted partly or completely         halogenated; phenyl and phenyl-C₁-C₆ alkyl,     -   wherein phenyl in the last 2 mentioned radical is unsubstituted         or substituted by 1, 2, 3, 4, or 5 identical or different         substituents selected from the group consisting of halogen, CN,         NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and         C₁-C₆-haloalkoxy;     -   in particular H, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,         (C₁-C₆-alkyl)carbonyl, (C₃-C₆-cycloalkyl)-carbonyl, or         (C₁-C₆-alkyl)sulfonyl;     -   more particularly H, CN, C₁-C₄-alkyl,         (C₁-C₄-alkoxy)-C₁-C₄-alkyl, (C₁-C₄-alkyl)carbonyl,         (C₃-C₆-cycloalkyl)-carbonyl, or (C₁-C₄-alkyl)sulfonyl;     -   even more particularly H, CN, CH₃, CH₂OCH₃, C(O)CH₃,         C(O)cyclopropyl or SO₂CH₃;     -   especially hydrogen.

Among the compounds of formula (I) further particular groups (1) of embodiments relate to the diaminotriazine compounds of formula (I), wherein

-   X is CR³R⁴R⁵, wherein R³, R⁴, R⁵ have the meaning defined above,

Also preferred are diaminotriazine compounds of formula (I), wherein

-   R³ is selected from the group consisting of H, halogen, CN,     C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, in     particular from the group consisting of hydrogen, fluorine,     chlorine, C₁-C₄-alkyl, such as methyl, ethyl, n-propyl, 2-propyl,     n-butyl, 2-butyl, isobutyl or tert.-butyl, C₁-C₄-haloalkyl, such as     difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl,     1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl,     C₁-C₄-alkoxy, such as methoxy or ethoxy and C₁-C₄-haloalkoxy, such     as difluoromethoxy or trifluoromethoxy.

Further particular groups (1) of embodiments relate to the diaminotriazine compounds of formula (I), wherein

-   R⁴ is selected from the group consisting of H, halogen, CN,     C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, in     particular from the group consisting of hydrogen, fluorine and     C₁-C₄-alkyl, more particularly from hydrogen, fluorine and methyl,     especially from hydrogen and fluorine.     In groups (1) of embodiments, R⁵ is as defined above. Preferably -   R⁵ is selected from the group consisting of C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl,     C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy and C₁-C₆-alkoxy-C₁-C₆-alkyl or     from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl,     C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy and     C₁-C₆-alkoxy-C₁-C₆-alkyl. In groups (1) of embodiments, R⁵ is in     particular selected from the group consisting of methyl,     C₂-C₄-alkyl, such as ethyl, n-propyl, 2-propyl, n-butyl, 2-butyl,     isobutyl or tert.-butyl, C₁-C₄-haloalkyl, such as difluoromethyl,     trifluoromethyl, 2,2,2-trifluoroethyl, 1,1-difluoroethyl,     1,1,2,2-tetrafluoroethyl or pentafluoroethyl, C₂-C₄-alkenyl, such as     vinyl or allyl, C₃-C₄-alkynyl, such as propargyl, C₃-C₆-cycloalkyl,     such as cyclopropyl, cyclobutyl, cylopentyl or cyclohexyl, and     C₁-C₄-alkoxy-C₁-C₄-alkyl, such as methoxymethyl, ethoxymethyl,     2-methoxyethyl or 2-ethoxyethyl.

Further particular groups (2) of embodiments relate to the diaminotriazine compounds of formula (I), wherein R⁴ and R⁵ together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, C₃-C₆-cycloalkan-1,1-diyl, ipso-C₃-C₆-cycloalkendiyl, three- to six-membered saturated or partially unsaturated ipso-heterocyclodiyl, where the carbocycle and the heterocycle are unsubstituted, partly or completely halogenated or carry from 1 to 6 C₁-C₆-alkyl groups, and the moiety >C═CR^(x)R^(y), where R^(x) and R^(y) are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

In groups (2) of embodiments, R⁴ and R⁵ together with the carbon atom to which they are attached form in particular a moiety selected from the group consisting of C₃-C₆-cycloalkan-1,1-diyl, ipso-C₃-C₆-cycloalkendiyl, three- to six-membered saturated or partially unsaturated ipso-heterocyclodiyl, where the carbocycle and the heterocycle are unsubstituted, partly or completely halogenated or carry from 1 to 6 C₁-C₆-alkyl groups and where the heterocycle preferably has 1 or 2 oxygen atoms as ring members.

In groups (2) of embodiments, R⁴ and R⁵ together with the carbon atom to which they are attached more particularly form a moiety selected from the group consisting of C₃-C₆-cycloalkan-1,1-diyl or three- to six-membered saturated ipso-heterocyclodiyl, where the carbocycle and the heterocycle are unsubstituted, partly or completely halogenated or carry from 1 to 6 C₁-C₆-alkyl groups, and where heterocyclyl preferably has 1 or 2 oxygen atoms as ring members.

Further particular groups (2a) of embodiments relate to the diaminotriazine compounds of formula (I), wherein R⁴ and R⁵ together with the carbon atom to which they are attached form C₃-C₆-cycloalkan-1,1-diyl, in particular cyclopropan-1,1-diyl, cyclobutan-1,1-diyl, cyclopentan-1,1-diyl or cyclohexan-1,1-diyl, said C₃-C₆-cycloalkan-1,1-diyl being unsubstituted, partly or completely halogenated or carrying from 1 to 6 C₁-C₆-alkyl groups, in particular methyl groups. In groups (2a) of embodiments R⁴ and R⁵ together with the carbon atom to which they are attached form in particular C₃-C₆-cycloalkan-1,1-diyl which is unsubstituted.

Further particular groups (2b) of embodiments relate to the diaminotriazine compounds of formula (I), wherein R⁴ and R⁵ together with the carbon atom to which they are attached form three- to six-membered saturated ipso-heterocyclodiyl, in particular oxiran-1,1-diyl, oxiran-2,2-diyl, oxetan-1,1-diyl, oxetan-2,2-diyl, oxetan-3,3-diyl, oxan-1,1-diyl, oxan-2,2-diyl or oxan-4,4-diyl, said heterocycle being unsubstituted, partly or completely halogenated or carrying from 1 to 6 C₁-C₆-alkyl groups, in particular groups, and where said heterocycle preferably has 1 or 2 oxygen atoms as ring members. In groups (2b) of embodiments R⁴ and R⁵ together with the carbon atom to which they are attached form three- to six-membered saturated ipso-heterocyclodiyl, in particular oxiran-2,2-diyl, oxetan-2,2-diyl, oxetan-3,3-diyl, oxan-2,2-diyl, or oxan-4,4-diyl, said heterocycle being unsubstituted.

Especially preferred examples of CR³R⁴R⁵ are those radicals, where R³, R⁴ and R⁵ are given in rows 1 to 64 of table 1a.

TABLE 1a no. R³ R⁴ R⁵ 1. H CH₃ CH₃ 2. F F CH₃ 3. F H CH₃ 4. F CH₃ CH₃ 5. CH₃ CH₃ CH₃ 6. F H C₂H₅ 7. H CH₃ C₂H₅ 8. F CH₃ C₂H₅ 9. H OCH₃ CH₃ 10. H OCH₃ C₂H₅ 11. F C₂H₅ C₂H₅ 12. H OCH₃ C₂H₅ 13. H H CH(CH₃)₂ 14. H F CH(CH₃)₂ 15. F F CH(CH₃)₂ 16. H CH₃ CH(CH₃)₂ 17. H OCH₃ CH(CH₃)₂ 18. F CH₃ CH(CH₃)₂ 19. H H CH₂CH₂CH₃ 20. H F CH₂CH₂CH₃ 21. F F CH₂CH₂CH₃ 22. H CH₃ CH₂CH₂CH₃ 23. H OCH₃ CH₂CH₂CH₃ 24. F CH₃ CH₂CH₂CH₃ 25. H H C(CH₃)₃ 26. H F C(CH₃)₃ 27. F F C(CH₃)₃ 28. H CH₃ C(CH₃)₃ 29. H OCH₃ C(CH₃)₃ 30. F CH₃ C(CH₃)₃ 31. H H Cyclopropyl 32. H F Cyclopropyl 33. F F Cyclopropyl 34. H CH₃ Cyclopropyl 35. H OCH₃ Cyclopropyl 36. F CH₃ Cyclopropyl 37. H CH₃ CF₃ 38. F CH₃ CF₃ 39. H CH₂—CH₂ 40. CH₃ CH₂—CH₂ 41. OCH₃ CH₂—CH₂ 42. F CH₂—CH₂ 43. Cl CH₂—CH₂ 44. H CH₂—CH₂—CH₂ 45. CH₃ CH₂—CH₂—CH₂ 46. OCH₃ CH₂—CH₂—CH₂ 47. F CH₂—CH₂—CH₂ 48. Cl CH₂—CH₂—CH₂ 49. H CH₂—CH₂—CH₂—CH₂ 50. CH₃ CH₂—CH₂—CH₂—CH₂ 51. OCH₃ CH₂—CH₂—CH₂—CH₂ 52. F CH₂—CH₂—CH₂—CH₂ 53. Cl CH₂—CH₂—CH₂—CH₂ 54. H CH₂—CH₂—CH₂—CH₂—CH₂ 55. CH₃ CH₂—CH₂—CH₂—CH₂—CH₂ 56. OCH₃ CH₂—CH₂—CH₂—CH₂—CH₂ 57. F CH₂—CH₂—CH₂—CH₂—CH₂ 58. Cl CH₂—CH₂—CH₂—CH₂—CH₂ 59. H O—CH₂—CH₂—CH₂ 60. CH₃ O—CH₂—CH₂—CH₂ 61. OCH₃ O—CH₂—CH₂—CH₂ 62. H O—CH₂—CH₂—CH₂—CH₂ 63. CH₃ O—CH₂—CH₂—CH₂—CH₂ 64. OCH₃ O—CH₂—CH₂—CH₂—CH₂

Further particular groups (3) of embodiments relate to the diaminotriazine compounds of formula (I), wherein

-   X is phenyl which is unsubstituted or may carry, 1, 2, 3, 4 or 5     radicals R^(Ar) as defined above, which are     -   in particular selected from the group consisting of halogen, CN,         C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)methoxy, C₂-C₆-alkynyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyloxy, C₂-C₆-alkenyloxy,         C₁-C₆-haloalkoxy;     -   wherein R^(Ar) is more particular selected from the group         consisting of halogen, C₁-C₄-alkyl, C₂-C₄-alkynyl,         C₂-C₄-alkynyloxy, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,         C₁-C₄-haloalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         (C₃-C₆-cycloalkyl)methoxy, CN; wherein R^(Ar) is especially         selected from the group consisting of F, Cl, methoxy, ethoxy,         CN;     -   Especially preferred examples for X is substituted or an         substituted phenyl are given in rows 1 to 563 of table 2a.

TABLE 2a no. X 1. C₆H₅ 2. 2-F—C₆H₄ 3. 3-F—C₆H₄ 4. 4-F—C₆H₄ 5. 2-Cl—C₆H₄ 6. 3-Cl—C₆H₄ 7. 4-Cl—C₆H₄ 8. 2-Br—C₆H₄ 9. 3-Br—C₆H₄ 10. 4-Br—C₆H₄ 11. 2-I—C₆H₄ 12. 3-I—C₆H₄ 13. 4-I—C₆H₄ 14. 2-CN—C₆H₄ 15. 3-CN—C₆H₄ 16. 4-CN—C₆H₄ 17. 2-OCH₃—C₆H₄ 18. 3-OCH₃—C₆H₄ 19. 4-OCH₃—C₆H₄ 20. 2-OCH₂F—C₆H₄ 21. 3-OCH₂F—C₆H₄ 22. 4-OCH₂F—C₆H₄ 23. 2-OCH₂F—C₆H₄ 24. 3-OCH₂F—C₆H₄ 25. 4-OCH₂F—C₆H₄ 26. 2-OCHF₂—C₆H₄ 27. 3-OCHF₂—C₆H₄ 28. 4-OCHF₂—C₆H₄ 29. 2-OCF₃—C₆H₄ 30. 3-OCF₃—C₆H₄ 31. 4-OCF₃—C₆H₄ 32. 3-OCH₂Cl—C₆H₄ 33. 4-OCH₂Cl—C₆H₄ 34. 2-OCH₂Cl—C₆H₄ 35. 3-OCH₂Cl—C₆H₄ 36. 4-OCH₂Cl—C₆H₄ 37. 2-OCHCl₂—C₆H₄ 38. 3-OCHCl₂—C₆H₄ 39. 4-OCHCl₂—C₆H₄ 40. 2-OCCl₃—C₆H₄ 41. 3-OCCl₃—C₆H₄ 42. 4-OCCl₃—C₆H₄ 43. 2-CH₂CH₃—C₆H₄ 44. 3-CH₂CH₃—C₆H₄ 45. 4-CH₂CH₃—C₆H₄ 46. 2-CF₂CHF₂—C₆H₄ 47. 3-CF₂CHF₂—C₆H₄ 48. 4-CF₂CHF₂—C₆H₄ 49. 2,3-F₂—C₆H₃ 50. 2,4-F₂—C₆H₃ 51. 2,5-F₂—C₆H₃ 52. 2,6-F₂—C₆H₃ 53. 3,4-F₂—C₆H₃ 54. 3,5-F₂—C₆H₃ 55. 2,3-Cl₂—C₆H₃ 56. 2,4-Cl₂—C₆H₃ 57. 2,5-Cl₂—C₆H₃ 58. 2,6-Cl₂—C₆H₃ 59. 3,4-Cl₂—C₆H₃ 60. 3,5-Cl₂—C₆H₃ 61. 2,3-Br₂—C₆H₃ 62. 2,4-Br₂—C₆H₃ 63. 2,5-Br₂—C₆H₃ 64. 2,6-Br₂—C₆H₃ 65. 3,4-Br₂—C₆H₃ 66. 3,5-Br₂—C₆H₃ 67. 2,3-I₂—C₆H₃ 68. 2,4-I₂—C₆H₃ 69. 2,5-I₂—C₆H₃ 70. 2,6-I₂—C₆H₃ 71. 3,4-I₂—C₆H₃ 72. 3,5-I₂—C₆H₃ 73. 2,3-(OCH₃)₂—C₆H₃ 74. 2,4-(OCH₃)₂—C₆H₃ 75. 2,5-(OCH₃)₂—C₆H₃ 76. 2,6-(OCF₃)₂—C₆H₃ 77. 3,4-(OCF₃)₂—C₆H₃ 78. 3,5-(OCH₃)₂—C₆H₃ 79. 2-F-3-Cl—C₆H₃ 80. 2-F-4-Cl—C₆H₃ 81. 2-F-5-Cl—C₆H₃ 82. 2-F-6-Cl—C₆H₃ 83. 3-F-2-Cl—C₆H₃ 84. 3-F-4-Cl—C₆H₃ 85. 3-F-5-Cl—C₆H₃ 86. 3-F-6-Cl—C₆H₃ 87. 4-F-2-Cl—C₆H₃ 88. 4-F-3-Cl—C₆H₃ 89. 4-F-5-Cl—C₆H₃ 90. 4-F-6-Cl—C₆H₃ 91. 2-F-3-Br—C₆H₃ 92. 2-F-4-Br—C₆H₃ 93. 2-F-5-Br—C₆H₃ 94. 2-F-6-Br—C₆H₃ 95. 3-F-2-Br—C₆H₃ 96. 3-F-4-Br—C₆H₃ 97. 3-F-5-Br—C₆H₃ 98. 3-F-6-Br—C₆H₃ 99. 4-F-2-Br—C₆H₃ 100. 4-F-3-Br—C₆H₃ 101. 4-F-5-Br—C₆H₃ 102. 4-F-6-Br—C₆H₃ 103. 2-F-3-I—C₆H₃ 104. 2-F-4-I—C₆H₃ 105. 2-F-5-I—C₆H₃ 106. 2-F-6-I—C₆H₃ 107. 3-F-2-I—C₆H₃ 108. 3-F-4-I—C₆H₃ 109. 3-F-5-I—C₆H₃ 110. 3-F-6-I—C₆H₃ 111. 4-F-2-I—C₆H₃ 112. 4-F-3-I—C₆H₃ 113. 4-F-5-I—C₆H₃ 114. 4-F-6-I—C₆H₃ 115. 2-F-3-OCH₃—C₆H₃ 116. 2-F-4-OCH₃—C₆H₃ 117. 2-F-5-OCH₃—C₆H₃ 118. 2-F-6-OCH₃—C₆H₃ 119. 3-F-2-OCH₃—C₆H₃ 120. 3-F-4-OCH₃—C₆H₃ 121. 3-F-5-OCH₃—C₆H₃ 122. 3-F-6-OCH₃—C₆H₃ 123. 4-F-2-OCH₃—C₆H₃ 124. 4-F-3-OCH₃—C₆H₃ 125. 4-F-5-OCH₃—C₆H₃ 126. 4-F-6-OCH₃—C₆H₃ 127. 2-F-3-OCF₃—C₆H₃ 128. 2-F-4-OCF₃—C₆H₃ 129. 2-F-5-OCF₃—C₆H₃ 130. 2-F-6-OCF₃—C₆H₃ 131. 3-F-2-OCF₃—C₆H₃ 132. 3-F-4-OCF₃—C₆H₃ 133. 3-F-5-OCF₃—C₆H₃ 134. 3-F-6-OCF₃—C₆H₃ 135. 4-F-2-OCF₃—C₆H₃ 136. 4-F-3-OCF₃—C₆H₃ 137. 4-F-5-OCF₃—C₆H₃ 138. 4-F-6-OCF₃—C₆H₃ 139. 2-F-3-CF₃—C₆H₃ 140. 2-F-4-CF₃—C₆H₃ 141. 2-F-5-CF₃—C₆H₃ 142. 2-F-6-CF₃—C₆H₃ 143. 3-F-2-CF₃—C₆H₃ 144. 3-F-4-CF₃—C₆H₃ 145. 3-F-5-CF₃—C₆H₃ 146. 3-F-6-CF₃—C₆H₃ 147. 4-F-2-CF₃—C₆H₃ 148. 4-F-3-CF₃—C₆H₃ 149. 4-F-5-CF₃—C₆H₃ 150. 4-F-6-CF₃—C₆H₃ 151. 2-Cl-3-F—C₆H₃ 152. 2-Cl-4-F—C₆H₃ 153. 2-Cl-5-F—C₆H₃ 154. 2-Cl-6-F—C₆H₃ 155. 3-Cl-2-F—C₆H₃ 156. 3-Cl-4-F—C₆H₃ 157. 3-Cl-5-F—C₆H₃ 158. 3-Cl-6-F—C₆H₃ 159. 4-Cl-2-F—C₆H₃ 160. 4-Cl-3-F—C₆H₃ 161. 4-Cl-5-F—C₆H₃ 162. 4-Cl-6-F—C₆H₃ 163. 2-Cl-3-Br—C₆H₃ 164. 2-Cl-4-Br—C₆H₃ 165. 2-Cl-5-Br—C₆H₃ 166. 2-Cl-6-Br—C₆H₃ 167. 3-Cl-2-Br—C₆H₃ 168. 3-Cl-4-Br—C₆H₃ 169. 3-Cl-5-Br—C₆H₃ 170. 3-Cl-6-Br—C₆H₃ 171. 4-Cl-2-Br—C₆H₃ 172. 4-Cl-3-Br—C₆H₃ 173. 4-Cl-5-Br—C₆H₃ 174. 4-Cl-6-Br—C₆H₃ 175. 2-Cl-3-I—C₆H₃ 176. 2-Cl-4-I—C₆H₃ 177. 2-Cl-5-I—C₆H₃ 178. 2-Cl-6-I—C₆H₃ 179. 3-Cl-2-I—C₆H₃ 180. 3-Cl-4-I—C₆H₃ 181. 3-Cl-5-I—C₆H₃ 182. 3-Cl-6-I—C₆H₃ 183. 4-Cl-2-I—C₆H₃ 184. 4-Cl-3-I—C₆H₃ 185. 4-Cl-5-I—C₆H₃ 186. 4-Cl-6-I—C₆H₃ 187. 2-Cl-3-OCH₃—C₆H₃ 188. 2-Cl-4-OCH₃—C₆H₃ 189. 2-Cl-5-OCH₃—C₆H₃ 190. 2-Cl-6-OCH₃—C₆H₃ 191. 3-Cl-2-OCH₃—C₆H₃ 192. 3-Cl-4-OCH₃—C₆H₃ 193. 3-Cl-5-OCH₃—C₆H₃ 194. 3-Cl-6-OCH₃—C₆H₃ 195. 4-Cl-2-OCH₃—C₆H₃ 196. 4-Cl-3-OCH₃—C₆H₃ 197. 4-Cl-5-OCH₃—C₆H₃ 198. 4-Cl-6-OCH₃—C₆H₃ 199. 2-Cl-3-OCF₃—C₆H₃ 200. 2-Cl-4-OCF₃—C₆H₃ 201. 2-Cl-5-OCF₃—C₆H₃ 202. 2-Cl-6-OCF₃—C₆H₃ 203. 3-Cl-2-OCF₃—C₆H₃ 204. 3-Cl-4-OCF₃—C₆H₃ 205. 3-Cl-5-OCF₃—C₆H₃ 206. 3-Cl-6-OCF₃—C₆H₃ 207. 4-Cl-2-OCF₃—C₆H₃ 208. 4-Cl-3-OCF₃—C₆H₃ 209. 4-Cl-5-OCF₃—C₆H₃ 210. 4-Cl-6-OCF₃—C₆H₃ 211. 2-Br-3-F—C₆H₃ 212. 2-Br-4-F—C₆H₃ 213. 2-Br-5-F—C₆H₃ 214. 2-Br-6-F—C₆H₃ 215. 3-Br-2-F—C₆H₃ 216. 3-Br-4-F—C₆H₃ 217. 3-Br-5-F—C₆H₃ 218. 3-Br-6-F—C₆H₃ 219. 4-Br-2-F—C₆H₃ 220. 4-Br-3-F—C₆H₃ 221. 4-Br-5-F—C₆H₃ 222. 4-Br-6-F—C₆H₃ 223. 2-Br-3-Cl—C₆H₃ 224. 2-Br-4-Cl—C₆H₃ 225. 2-Br-5-Cl—C₆H₃ 226. 2-Br-6-Cl—C₆H₃ 227. 3-Br-2-Cl—C₆H₃ 228. 3-Br-4-Cl—C₆H₃ 229. 3-Br-5-Cl—C₆H₃ 230. 3-Br-6-Cl—C₆H₃ 231. 4-Br-2-Cl—C₆H₃ 232. 4-Br-3-Cl—C₆H₃ 233. 4-Br-5-Cl—C₆H₃ 234. 4-Br-6-Cl—C₆H₃ 235. 2-Br-3-I—C₆H₃ 236. 2-Br-4-I—C₆H₃ 237. 2-Br-5-I—C₆H₃ 238. 2-Br-6-I—C₆H₃ 239. 3-Br-2-I—C₆H₃ 240. 3-Br-4-I—C₆H₃ 241. 3-Br-5-I—C₆H₃ 242. 3-Br-6-I—C₆H₃ 243. 4-Br-2-I—C₆H₃ 244. 4-Br-3-I—C₆H₃ 245. 4-Br-5-I—C₆H₃ 246. 4-Br-6-I—C₆H₃ 247. 2-Br-3-OCH₃—C₆H₃ 248. 2-Br-4-OCH₃—C₆H₃ 249. 2-Br-5-OCH₃—C₆H₃ 250. 2-Br-6-OCH₃—C₆H₃ 251. 3-Br-2-OCH₃—C₆H₃ 252. 3-Br-4-OCH₃—C₆H₃ 253. 3-Br-5-OCH₃—C₆H₃ 254. 3-Br-6-OCH₃—C₆H₃ 255. 4-Br-2-OCH₃—C₆H₃ 256. 4-Br-3-OCH₃—C₆H₃ 257. 4-Br-5-OCH₃—C₆H₃ 258. 4-Br-6-OCH₃—C₆H₃ 259. 2-Br-3-OCF₃—C₆H₃ 260. 2-Br-4-OCF₃—C₆H₃ 261. 2-Br-5-OCF₃—C₆H₃ 262. 2-Br-6-OCF₃—C₆H₃ 263. 3-Br-2-OCF₃—C₆H₃ 264. 3-Br-4-OCF₃—C₆H₃ 265. 3-Br-5-OCF₃—C₆H₃ 266. 3-Br-6-OCF₃—C₆H₃ 267. 4-Br-2-OCF₃—C₆H₃ 268. 4-Br-3-OCF₃—C₆H₃ 269. 4-Br-5-OCF₃—C₆H₃ 270. 4-Br-6-OCF₃—C₆H₃ 271. 2,3,4-F₃—C₆H₂ 272. 2,3,5-F₃—C₆H₂ 273. 2,3,6-F₃—C₆H₂ 274. 2,4,5-F₃—C₆H₂ 275. 2,4,6-F₃—C₆H₂ 276. 3,4,5-F₃—C₆H₂ 277. 2,3,4-Cl₃—C₆H₂ 278. 2,3,5-Cl₃—C₆H₂ 279. 2,3,6-Cl₃—C₆H₂ 280. 2,4,5-Cl₃—C₆H₂ 281. 2,4,6-Cl₃—C₆H₂ 282. 3,4,5-Cl₃—C₆H₂ 283. 2,3,4-Br₃—C₆H₂ 284. 2,3,5-Br₃—C₆H₂ 285. 2,3,6-Br₃—C₆H₂ 286. 2,4,5-Br₃—C₆H₂ 287. 2,4,6-Br₃—C₆H₂ 288. 3,4,5-Br₃—C₆H₂ 289. 2,3,4-(OCH₃)₃—C₆H₂ 290. 2,3,5-(OCH₃)₃—C₆H₂ 291. 2,3,6-(OCH₃)₃—C₆H₂ 292. 2,4,5-(OCH₃)₃—C₆H₂ 293. 2,4,6-(OCH₃)₃—C₆H₂ 294. 3,4,5-(OCH₃)₃—C₆H₂ 295. 2,3-F₂-4-Cl—C₆H₂ 296. 2,3-F₂-5-Cl—C₆H₂ 297. 2,3-F₂-6-Cl—C₆H₂ 298. 2,4-F₂-3-Cl—C₆H₂ 299. 2,4-F₂-5-Cl—C₆H₂ 300. 2,4-F₂-6-Cl—C₆H₂ 301. 2,5-F₂-3-Cl—C₆H₂ 302. 2,5-F₂-4-Cl—C₆H₂ 303. 2,5-F₂-6-Cl—C₆H₂ 304. 2,6-F₂-3-Cl—C₆H₂ 305. 2,6-F₂-4-Cl—C₆H₂ 306. 2,3-F₂-4-Br—C₆H₂ 307. 2,3-F₂-5-Br—C₆H₂ 308. 2,3-F₂-6-Br—C₆H₂ 309. 2,4-F₂-3-Br—C₆H₂ 310. 2,4-F₂-5-Br—C₆H₂ 311. 2,4-F₂-6-Br—C₆H₂ 312. 2,5-F₂-3-Br—C₆H₂ 313. 2,5-F₂-4-Br—C₆H₂ 314. 2,5-F₂-6-Br—C₆H₂ 315. 2,6-F₂-3-Br—C₆H₂ 316. 2,6-F₂-4-Br—C₆H₂ 317. 2,3-F₂-4-OCH₃—C₆H₂ 318. 2,3-F₂-5-OCH₃—C₆H₂ 319. 2,3-F₂-6-OCH₃—C₆H₂ 320. 2,4-F₂-3-OCH₃—C₆H₂ 321. 2,4-F₂-5-OCH₃—C₆H₂ 322. 2,4-F₂-6-OCH₃—C₆H₂ 323. 2,5-F₂-3-OCH₃—C₆H₂ 324. 2,5-F₂-4-OCH₃—C₆H₂ 325. 2,5-F₂-6-OCH₃—C₆H₂ 326. 2,6-F₂-3-OCH₃—C₆H₂ 327. 2,6-F₂-4-OCH₃—C₆H₂ 328. 2,3-Cl₂-4-F—C₆H₂ 329. 2,3-Cl₂-5-F—C₆H₂ 330. 2,3-Cl₂-6-F—C₆H₂ 331. 2,4-Cl₂-3-F—C₆H₂ 332. 2,4-Cl₂-5-F—C₆H₂ 333. 2,4-Cl₂-6-F—C₆H₂ 334. 2,5-Cl₂-3-F—C₆H₂ 335. 2,5-Cl₂-4-F—C₆H₂ 336. 2,5-Cl₂-6-F—C₆H₂ 337. 2,6-Cl₂-3-F—C₆H₂ 338. 2,6-Cl₂-4-F—C₆H₂ 339. 2,3-Cl₂-4-Br—C₆H₂ 340. 2,3-Cl₂-5-Br—C₆H₂ 341. 2,3-Cl₂-6-Br—C₆H₂ 342. 2,4-Cl₂-3-Br—C₆H₂ 343. 2,4-Cl₂-5-Br—C₆H₂ 344. 2,4-Cl₂-6-Br—C₆H₂ 345. 2,5-Cl₂-3-Br—C₆H₂ 346. 2,5-Cl₂-4-Br—C₆H₂ 347. 2,5-Cl₂-6-Br—C₆H₂ 348. 2,6-Cl₂-3-Br—C₆H₂ 349. 2,6-Cl₂-4-Br—C₆H₂ 350. 2,3-Cl₂-4-OCH₃—C₆H₂ 351. 2,3-Cl₂-5-OCH₃—C₆H₂ 352. 2,3-Cl₂-6-OCH₃—C₆H₂ 353. 2,4-Cl₂-3-OCH₃—C₆H₂ 354. 2,4-Cl₂-5-OCH₃—C₆H₂ 355. 2,4-Cl₂-6-OCH₃—C₆H₂ 356. 2,5-Cl₂-3-OCH₃—C₆H₂ 357. 2,5-Cl₂-4-OCH₃—C₆H₂ 358. 2,5-Cl₂-6-OCH₃—C₆H₂ 359. 2,6-Cl₂-3-OCH₃—C₆H₂ 360. 2,6-Cl₂-4-OCH₃—C₆H₂ 361. 2,3-Br₂-4-F—C₆H₂ 362. 2,3-Br₂-5-F—C₆H₂ 363. 2,3-Br₂-6-F—C₆H₂ 364. 2,4-Br₂-3-F—C₆H₂ 365. 2,4-Br₂-5-F—C₆H₂ 366. 2,4-Br₂-6-F—C₆H₂ 367. 2,5-Br₂-3-F—C₆H₂ 368. 2,5-Br₂-4-F—C₆H₂ 369. 2,5-Br₂-6-F—C₆H₂ 370. 2,6-Br₂-3-F—C₆H₂ 371. 2,6-Br₂-4-F—C₆H₂ 372. 2,3-Br₂-4-Cl—C₆H₂ 373. 2,3-Br₂-5-Cl—C₆H₂ 374. 2,3-Br₂-6-Cl—C₆H₂ 375. 2,4-Br₂-3-Cl—C₆H₂ 376. 2,4-Br₂-5-Cl—C₆H₂ 377. 2,4-Br₂-6-Cl—C₆H₂ 378. 2,5-Br₂-3-Br—C₆H₂ 379. 2,5-Br₂-4-Cl—C₆H₂ 380. 2,5-Br₂-6-Cl—C₆H₂ 381. 2,6-Br₂-Cl—C₆H₂ 382. 2,6-Br₂-4-Cl—C₆H₂ 383. 2,3-Br₂-4-OCH₃—C₆H₂ 384. 2,3-Br₂-5-OCH₃—C₆H₂ 385. 2,3-Br₂-6-OCH₃—C₆H₂ 386. 2,4-Br₂-3-OCH₃—C₆H₂ 387. 2,4-Br₂-5-OCH₃—C₆H₂ 388. 2,4-Br₂-6-OCH₃—C₆H₂ 389. 2,5-Br₂-3-OCH₃—C₆H₂ 390. 2,5-Br₂-4-OCH₃—C₆H₂ 391. 2,5-Br₂-6-OCH₃—C₆H₂ 392. 2,6-Br₂-3-OCH₃—C₆H₂ 393. 2,6-Br₂-4-OCH₃—C₆H₂ 394. 2-F-3-Cl-4-OCH₃—C₆H₂ 395. 2-F-3-Cl-5-OCH₃—C₆H₂ 396. 2-F-3-Cl-6-OCH₃—C₆H₂ 397. 2-F-5-Cl-4-OCH₃—C₆H₂ 398. 2-F-6-Cl-4-OCH₃—C₆H₂ 399. 2-F-3-OCH₃-4-Cl—C₆H₂ 400. 2-F-3-OCH₃-5-Cl—C₆H₂ 401. 2-F-3-OCH₃-6-Cl—C₆H₂ 402. 2-F-5-OCH₃-4-Cl—C₆H₂ 403. 2-F-6-OCH₃-4-Cl—C₆H₂ 404. 3-F-4-Cl-5-OCH₃—C₆H₂ 405. 3-F-2-Cl-5-OCH₃—C₆H₂ 406. 3-F-6-Cl-5-OCH₃—C₆H₂ 407. 3-F-4-Cl-2-OCH₃—C₆H₂ 408. 3-F-4-Cl-6-OCH₃—C₆H₂ 409. 3-F-4-OCH₃-5-Cl—C₆H₂ 410. 3-F-2-OCH₃-5-Cl—C₆H₂ 411. 3-F-6-OCH₃-5-Cl—C₆H₂ 412. 3-F-4-OCH₃-2-Cl—C₆H₂ 413. 3-F-4-OCH₃-6-Cl—C₆H₂ 414. 4-F-3-Cl-5-OCH₃—C₆H₂ 415. 4-F-3-Cl-2-OCH₃—C₆H₂ 416. 4-F-3-Cl-6-OCH₃—C₆H₂ 417. 4-F-2-Cl-5-OCH₃—C₆H₂ 418. 4-F-2-Cl-6-OCH₃—C₆H₂ 419. 4-F-3-OCH₃-5-Cl—C₆H₂ 420. 4-F-3-OCH₃-2-Cl—C₆H₂ 421. 4-F-3-OCH₃-6-Cl—C₆H₂ 422. 4-F-2-OCH₃-5-Cl—C₆H₂ 423. 4-F-2-OCH₃-6-Cl—C₆H₂ 424. 5-F-3-Cl-4-OCH₃—C₆H₂ 425. 5-F-3-Cl-2-OCH₃—C₆H₂ 426. 5-F-3-Cl-6-OCH₃—C₆H₂ 427. 5-F-2-Cl-4-OCH₃—C₆H₂ 428. 5-F-6-Cl-4-OCH₃—C₆H₂ 429. 5-F-3-OCH₃-4-Cl—C₆H₂ 430. 5-F-3-OCH₃-2-Cl—C₆H₂ 431. 5-F-3-OCH₃-6-Cl—C₆H₂ 432. 5-F-2-OCH₃-4-Cl—C₆H₂ 433. 5-F-6-OCH₃4-Cl—C₆H₂ 434. 6-F-5-Cl-4-OCH₃—C₆H₂ 435. 6-F-5-Cl-3-OCH₃—C₆H₂ 436. 6-F-5-Cl-2-OCH₃—C₆H₂ 437. 6-F-3-Cl-4-OCH₃—C₆H₂ 438. 6-F-2-Cl-4-OCH₃—C₆H₂ 439. 6-F-5-OCH₃-4-Cl—C₆H₂ 440. 6-F-5-OCH₃-3-Cl—C₆H₂ 441. 6-F-5-OCH₃-2-Cl—C₆H₂ 442. 6-F-3-OCH₃-4-Cl—C₆H₂ 443. 6-F-2-OCH₃-4-Cl—C₆H₂ 444. 2-Cl-3-F-4-OCH₃—C₆H₂ 445. 2-Cl-3-F-5-OCH₃—C₆H₂ 446. 2-Cl-3-F-6-OCH₃—C₆H₂ 447. 2-Cl-5-F-4-OCH₃—C₆H₂ 448. 2-Cl-6-F-4-OCH₃—C₆H₂ 449. 2-Cl-3-OCH₃-4-F—C₆H₂ 450. 2-Cl-3-OCH₃-5-F—C₆H₂ 451. 2-Cl-3-OCH₃-6-F—C₆H₂ 452. 2-Cl-5-OCH₃-4-F—C₆H₂ 453. 2-Cl-6-OCH₃-4-F—C₆H₂ 454. 3-Cl-4-F-5-OCH₃—C₆H₂ 455. 3-Cl-2-F-5-OCH₃—C₆H₂ 456. 3-Cl-6-F-5-OCH₃—C₆H₂ 457. 3-Cl-4-F-2-OCH₃—C₆H₂ 458. 3-Cl-4-F-6-OCH₃—C₆H₂ 459. 3-Cl-4-OCH₃-5-F—C₆H₂ 460. 3-Cl-2-OCH₃-5-F—C₆H₂ 461. 3-Cl-6-OCH₃-5-F—C₆H₂ 462. 3-Cl-4-OCH₃-2-F—C₆H₂ 463. 3-Cl-4-OCH₃-6-F—C₆H₂ 464. 4-Cl-3-F-5-OCH₃—C₆H₂ 465. 4-Cl-3-F-2-OCH₃—C₆H₂ 466. 4-Cl-3-F-6-OCH₃—C₆H₂ 467. 4-Cl-2-F-5-OCH₃—C₆H₂ 468. 4-Cl-2-F-6-OCH₃—C₆H₂ 469. 4-Cl-3-OCH₃-5-F—C₆H₂ 470. 4-Cl-3-OCH₃-2-F—C₆H₂ 471. 4-Cl-3-OCH₃-6-F—C₆H₂ 472. 4-Cl-2-OCH₃-5-F—C₆H₂ 473. 4-Cl-2-OCH₃-6-F—C₆H₂ 474. 5-Cl-3-F-4-OCH₃—C₆H₂ 475. 5-Cl-3-F-2-OCH₃—C₆H₂ 476. 5-Cl-3-F-6-OCH₃—C₆H₂ 477. 5-Cl-2-F-4-OCH₃—C₆H₂ 478. 5-Cl-6-F-4-OCH₃—C₆H₂ 479. 5-Cl-3-OCH₃-4-F—C₆H₂ 480. 5-Cl-3-OCH₃-2-F—C₆H₂ 481. 5-Cl-3-OCH₃-6-F—C₆H₂ 482. 5-Cl-2-OCH₃-4-F—C₆H₂ 483. 5-Cl-6-OCH₃4-F—C₆H₂ 484. 6-Cl-5-F-4-OCH₃—C₆H₂ 485. 6-Cl-5-F-3-OCH₃—C₆H₂ 486. 6-Cl-5-F-2-OCH₃—C₆H₂ 487. 6-Cl-3-F-4-OCH₃—C₆H₂ 488. 6-Cl-2-F-4-OCH₃—C₆H₂ 489. 6-Cl-5-OCH₃-4-F—C₆H₂ 490. 6-Cl-5-OCH₃-3-F—C₆H₂ 491. 6-Cl-5-OCH₃-2-F—C₆H₂ 492. 6-Cl-3-OCH₃-4-F—C₆H₂ 493. 6-Cl-2-OCH₃-4-F—C₆H₂ 494. 2-OCH₃-3-Cl-4-F—C₆H₂ 495. 2-OCH₃-3-Cl-5-F—C₆H₂ 496. 2-OCH₃-3-Cl-6-F—C₆H₂ 497. 2-OCH₃-5-Cl-4-F—C₆H₂ 498. 2-OCH₃-6-Cl-4-F—C₆H₂ 499. 2-OCH₃-3-F-4-Cl—C₆H₂ 500. 2-OCH₃-3-F-5-Cl—C₆H₂ 501. 2-OCH₃-3-F-6-Cl—C₆H₂ 502. 2-OCH₃-5-F-4-Cl—C₆H₂ 503. 2-OCH₃-6-F-4-Cl—C₆H₂ 504. 3-OCH₃-4-Cl-5-F—C₆H₂ 505. 3-OCH₃-2-Cl-5-F—C₆H₂ 506. 3-OCH₃-6-Cl-5-F—C₆H₂ 507. 3-OCH₃-4-Cl-2-F—C₆H₂ 508. 3-OCH₃-4-Cl-6-F—C₆H₂ 509. 3-OCH₃-4-F-5-Cl—C₆H₂ 510. 3-OCH₃-2-F-5-Cl—C₆H₂ 511. 3-OCH₃-6-F-5-Cl—C₆H₂ 512. 3-OCH₃-4-F-2-Cl—C₆H₂ 513. 3-OCH₃-4-F-6-Cl—C₆H₂ 514. 4-OCH₃-3-Cl-5-F—C₆H₂ 515. 4-OCH₃-3-Cl-2-F—C₆H₂ 516. 4-OCH₃-3-Cl-6-F—C₆H₂ 517. 4-OCH₃-2-Cl-5-F—C₆H₂ 518. 4-OCH₃-2-Cl-6-F—C₆H₂ 519. 4-OCH₃-3-F-5-Cl—C₆H₂ 520. 4-OCH₃-3-F-2-Cl—C₆H₂ 521. 4-OCH₃-3-F-6-Cl—C₆H₂ 522. 4-OCH₃-2-F-5-Cl—C₆H₂ 523. 4-OCH₃-2-F-6-Cl—C₆H₂ 524. 5-OCH₃-3-Cl-4-F—C₆H₂ 525. 5-OCH₃-3-Cl-2-F—C₆H₂ 526. 5-OCH₃-3-Cl-6-F—C₆H₂ 527. 5-OCH₃-2-Cl-4-F—C₆H₂ 528. 5-OCH₃-6-Cl-4-F—C₆H₂ 529. 5-OCH₃-3-F-4-Cl—C₆H₂ 530. 5-OCH₃-3-F-2-Cl—C₆H₂ 531. 5-OCH₃-3-F-6-Cl—C₆H₂ 532. 5-OCH₃-2-F-4-Cl—C₆H₂ 533. 5-OCH₃-6-F-4-Cl—C₆H₂ 534. 6-OCH₃-5-Cl-4-F—C₆H₂ 535. 6-OCH₃-5-Cl-3-F—C₆H₂ 536. 6-OCH₃-5-Cl-2-F—C₆H₂ 537. 6-OCH₃-3-Cl-4-F—C₆H₂ 538. 6-OCH₃-2-Cl-4-F—C₆H₂ 539. 6-OCH₃-5-F-4-Cl—C₆H₂ 540. 6-OCH₃-5-F-3-Cl—C₆H₂ 541. 6-OCH₃-5-F-2-Cl—C₆H₂ 542. 6-OCH₃-3-F-4-Cl—C₆H₂ 543. 6-OCH₃-2-F-4-Cl—C₆H₂ 544. 2,3,4,5-F₄—C₆H 545. 2,3,4,5-Cl₄—C₆H 546. 2,3,4,5-Br₄—C₆H 547. 2,3,4,5-(OCH₃)₄—C₆H 548. 2,3,5,6-F₄-4-Cl—C₆ 549. 2,4,5,6-F₄-3-Cl—C₆ 550. 2,3,4,6-F₄-5-Cl—C₆ 551. 2,3,4,5-F₄-6-Cl—C₆ 552. 3,4,5,6-F₄-2-Cl—C₆ 553. 2,3,5,6-F₄-4-Br—C₆ 554. 2,4,5,6-F₄-3-Br—C₆ 555. 2,3,4,6-F₄-5-Br—C₆ 556. 2,3,4,5-F₄-6-Br—C₆ 557. 3,4,5,6-F₄-2-Br—C₆ 558. 2,3,5,6-F₄-4-OCH₃—C₆ 559. 2,4,5,6-F₄-3-OCH₃—C₆ 560. 2,3,4,6-F₄-5-OCH₃—C₆ 561. 2,3,4,5-F₄-6-OCH₃—C₆ 562. 3,4,5,6-F₄-2-OCH₃—C₆ 563. 2,3,4,5,6-F₅—C₆

Further particular groups (4) of embodiments relate to the diaminotriazine compounds of formula (I), wherein

-   X is OR^(3c), where     -   R^(3c) is in particular selected from the group consisting of         C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl,         (C₁-C₆-alkyl)sulfonyl, where the aliphatic parts of the 6         aforementioned radicals unsubstituted, partly or completely         halogenated; phenyl, phenylsulfonyl or phenyl-C₁-C₆ alkyl,     -   wherein phenyl in the last 3 mentioned radicals is unsubstituted         or substituted by 1, 2, 3, 4 or 5 identical or different         substituents selected from the group consisting of halogen, CN,         NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and         C₁-C₆-haloalkoxy     -   more particularly from the group consisting of C₁-C₄-alkyl,         (C₁-C₄-alkoxy)-C₁-C₄-alkyl, C₃-C₄-cycloalkyl,         (C₁-C₄-alkyl)-carbonyl, (C₁-C₄-alkoxy)carbonyl,         (C₁-C₄-alkyl)sulfonyl, where the aliphatic parts of the 6         aforementioned radicals unsubstituted, partly or completely         halogenated;     -   especially C₁-C₄-alkyl, such as CH₃, CH₃CH₂, CH(CH₃)₂,         CH₂CH(CH₃)₂, C(CH₃)₃, or C₁-C₄-haloalkyl, such as CH₂CF₃,         CF(CH₃)₂, CH(CF₃)₂ or CH(CH₃)CF₃.     -   Further particular groups (5) of embodiments relate to the         diaminotriazine compounds of formula (I), wherein -   X is S(O)_(k)R^(3d), wherein k and R^(3d) are as defined above where     -   R^(3d) is in particular selected from the group consisting of H,         C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl,         (C₁-C₆-alkyl)sulfonyl, where the aliphatic parts of the 7         aforementioned radicals unsubstituted, partly or completely         halogenated; phenyl, phenylsulfonyl or phenyl-C₁-C₆ alkyl,     -   wherein phenyl in the last 3 mentioned radicals is unsubstituted         or substituted by 1, 2, 3, 4 or 5 identical or different         substituents selected from the group consisting of halogen, CN,         NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and         C₁-C₆-haloalkoxy     -   more particularly from the group consisting of C₁-C₄-alkyl,         (C₁-C₄-alkoxy)-C₁-C₄-alkyl, C₃-C₄-cycloalkyl,         (C₁-C₄-alkyl)-carbonyl, (C₁-C₄-alkoxy)carbonyl,         (C₁-C₄-alkyl)sulfonyl, where the aliphatic parts of the 6         aforementioned radicals unsubstituted, partly or completely         halogenated     -   especially C₁-C₄-alkyl, such as CH₃, CH₃CH₂, CH(CH₃)₂,         CH₂CH(CH₃)₂, C(CH₃)₃, or C₁-C₄-haloalkyl, such as CH₂CF₃,         CF(CH₃)₂, CH(CF₃)₂ or CH(CH₃)CF₃.

In this particular group (2) of embodiments, where X is S(O)_(k)R^(3d) the variable k is preferably 0 or 2 and especially 0.

Further particular groups (6) of embodiments relate to the diaminotriazine compounds of formula (I), wherein

-   X is NR^(3a)R^(3b), wherein R^(3a) and R^(3b) are as defined above     and wherein at least one of R^(3a) and R^(3b) is preferably     different from H, and where     -   R^(3a) R^(3b) are independently of one another H, CN, S(O)₂NH₂,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,         (C₁-C₆-alkyl)-carbonyl, (C₃-C₆-cycloalkyl)-carbonyl,         (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl,         C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl,         (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl and         (C₁-C₆-alkoxy)sulfonyl where the aliphatic parts of the 15         aforementioned radicals are unsubstituted, partly or completely         halogenated,     -   phenyl, phenylsulfonyl or phenyl-C₁-C₆ alkyl,     -   wherein phenyl in the last 3 mentioned radicals is unsubstituted         or substituted by 1, 2, 3, 4 or 5 identical or different         substituents selected from the group consisting of halogen, CN,         NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and         C₁-C₆-haloalkoxy,     -   one of R^(3a), R^(3b) may also be OH, C₁-C₆-alkoxy,         C₃-C₆-cycloalkoxy, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, where the         aliphatic and cycloaliphatic parts of the 3 aforementioned         radicals are unsubstituted, partly or completely halogenated; -   R^(3a) R^(3b) are independently of one another more particularly     selected from the group consisting of H, C₁-C₄-alkyl, such as CH₃,     CH₃CH₂, CH(CH₃)₂, CH₂CH(CH₃)₂, or C(CH₃)₃, C₁-C₄-haloalkyl, such as     CH₂CF₃, CF(CH₃)₂, CH(CF₃)₂ or CH(CH₃)CF₃, phenyl and phenyl-C₁-C₄     alkyl, such as benzyl, 1-phenylethyl or 2-phenylethyl, wherein     phenyl in phenyl and phenyl-C₁-C₄ alkyl is unsubstituted or     substituted by 1, 2, 3, 4 or 5 identical or different substituents     selected from the group consisting of halogen, CN, C₁-C₄-alkyl,     C₃-C₄-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and     C₁-C₄-haloalkoxy; -   especially from the group consisting of hydrogen, C₁-C₄-alkyl, such     as CH₃, CH₃CH₂, CH(CH₃)₂, CH₂CH(CH₃)₂, C(CH₃)₃, phenyl and benzyl.

Further particular groups of (6.a) embodiments relate to the diaminotriazine compounds of formula (I), wherein

-   X is NR^(3a)R^(3b), wherein     -   R^(3a), R^(3b) together with the nitrogen atom, to which they         are bound, form an N bound saturated or unsaturated mono- or         bicyclic heterocyclic radical, which may have 1, 2, 3 or 4, in         particular 1 or 2, further heteroatoms which are selected from         N, O and S, which heterocyclic radical is substituted or         unsubstituted by one or more, e. g. 1, 2, 3, 4, 5, 6, 7 or 8         identical or different substituents selected from the group         consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl and C₁-C₆-haloalkoxy,         in particular selected from the group consisting halogen, CN,         NO₂, C₁-C₂-alkyl, C₁-C₂-haloalkyl, (C₁-C₂-alkoxy)-C₁-C₂-alkyl,         C₁-C₂-alkoxy and C₁-C₂-haloalkoxy;     -   R^(3a), R^(3b) together with the nitrogen atom, to which they         are bound, in particular form an N bound saturated         monoheterocyclic radical, which may have 1 or 2 further         heteroatoms which are selected from N and O, which heterocyclic         radical is substituted or unsubstituted by one or more, e. g. 1,         2, 3, 4, 5, 6, 7 or 8 identical or different substituents         selected from the group consisting of halogen, CN, NO₂,         C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         (C₁-C₆-alkoxy)-C₁-C₆-alkyl and C₁-C₆-haloalkoxy, in particular         selected from the group consisting halogen, CN, NO₂,         C₁-C₂-alkyl, C₁-C₂-haloalkyl, (C₁-C₂-alkoxy)-C₁-C₂-alkyl,         C₁-C₂-alkoxy and C₁-C₂-haloalkoxy;     -   R^(3a), R^(3b) together with the nitrogen atom, to which they         are bound, more particularly form an N bound saturated mono- or         bicyclic heterocyclic radical, which is selected from the group         consisting of 1-aziridinyl, 1-azetidinyl, 1-piperidinyl,         1-pyrrolidinyl, azepan-1-yl, azocan-1-yl, morpholin-4-yl,         isoxazolidine-2-yl, oxazolidine-3-yl, piperazine-1-yl,         octahydroisoindol-2-yl, octahydroindol-1-yl,         octahydro-2H-quinolin-1-yl, azabicyclo[2.2.1]heptan-3-yl and         azabicyclo[2.2.1]heptan-7-yl, where the aforementioned radicals         are unsubstituted or substituted by one or more identical or         different substituents selected from the group consisting of         halogen, CN, NO₂, C₁-C₂-alkyl, C₁-C₂-haloalkyl,         (C₁-C₂-alkoxy)-C₁-C₂-alkyl, C₁-C₂-alkoxy and C₁-C₂-haloalkoxy;     -   R^(3a), R^(3b) together with the nitrogen atom, to which they         are bound, especially form an N-bound saturated monocyclic         heterocyclic radical, which is selected from the group         consisting of 1-piperidinyl, 1-pyrrolidinyl, azepan-1-yl,         azocan-1-yl, morpholin-4-yl, where the aforementioned radicals         are unsubstituted or substituted by one or more identical or         different substituents selected from the group consisting of         halogen, CN, NO₂, C₁-C₂-alkyl, C₁-C₂-haloalkyl,         (C₁-C₂-alkoxy)-C₁-C₂-alkyl, C₁-C₂-alkoxy and C₁-C₂-haloalkoxy.

Especially preferred examples of X, wherein X is NR^(3a)R^(3b), OR^(3c) or S(O)_(k)R^(3d) are given in rows 1 to 75 of table 3a.

TABLE 3a no. X 1 NH—CH₃ 2 N(CH₃)₂ 3 NH—C₂H₅ 4 N(CH₃) —C₂H₅ 5 N(C₂H₅)₂ 6 NH—CH(CH₃)₂ 7 NH—C(CH₃)₃ 8 NH—OCH₃ 9 N(CH₃)—OCH₃ 10 NH—OC₂H₅ 11 NH—C₆H₅ 12 NH—CH₂C₆H₅ 13 N(CH₃)C₆H₅ 14 N1 15 N2 16 N3 17 N4 18 N5 19 N6 20 N7 21 (R/S)-N8 22 (R)-N8 23 (S)-N8 24 E-N9 25 Z-N9 26 E-N10 27 Z-N10 28 N11 29 N12 30 N13 31 (R/S)-N14 32 (R)-N14 33 (S)-N14 34 O—CH₃ 35 O—C₂H₅ 36 O—CH₂CF₃ 37 O—CH(CH₃)₂ 38 O—C(CH₃)₃ 39 O—CH(C₂H₅)₂ 40 O—CH₂CH(CH₃)₂ 41 O—CH(CH₃)(CF₃) 42 O—CF(CH₃)₂ 43 O—C(CF₃)(CH₃)₂ 44 O—CH₂OCH₃ 45 O—CH₂CH₂OCH₃ 46 O—C₆H₅ 47 O—c-C₃H₅ 48 O—c-C₅H₉ 49 O—c-C₆H₁₁ 50 O—O1 51 O—O2 52 O—O3 53 O—CH₂-c-C₃H₅ 54 O—CH₂-c-C₅H₉ 55 S—CH₃ 56 S—C₂H₅ 57 S—CH₂CF₃ 58 S—CH(CH₃)₂ 59 S—C(CH₃)₃ 60 S—CH(C₂H₅)₂ 61 S—CH₂CH(CH₃)₂ 62 S—CH(CH₃)(CF₃) 63 S—CF(CH₃)₂ 64 S—C(CF₃)(CH₃)₂ 65 S—CH₂OCH₃ 66 S—CH₂CH₂OCH₃ 67 S—C₆H₅ 68 S—c-C₃H₅ 69 S—c-C₅H₉ 70 S—c-C₆H₁₁ 71 S—O1 72 S—O2 73 S—O3 74 S—CH₂—c-C₃H₅ 75 S—CH₂—c-C₅H₉

In table 3a the abbreviations given in the following table A1 are used:

TABLE A1 c-C₃H₅ cyclopropyl c-C₅H₉ cyclopentyl c-C₆H₁₁ cyclohexyl C₆H₅ Phenyl N1 azetidin-1-yl N2 aziridin-1-yl N3 pyrrolidin-1-yl N4 piperidin-1-yl N5 azepan-1-yl N6 azocan-1-yl N7 azonan-1-yl (R/S)-N8 (R/S)-2-methylpyrrolidin-1-yl (R)-N8 (R)-2-methylpyrrolidin-1-yl (S)-N8 (S)-2-methylpyrrolidin-1-yl E-N9 E-2,5-dimethylpyrrolidin-1-yl Z-N9 Z-2,5-dimethylpyrrolidin-1-yl E-N10 E-3,5-dimethylpiperidin-1-yl Z-N10 S-3,5-dimethylpiperidin-1-yl N11 morpholin-4-yl N12 4-methylpiperazin-1-yl N13 Isoxazolidin-2-yl (R/S)-N14 (2R)-2-(methoxymethyl)pyrrolidin-1-yl (R)-N14 (2S)-2-(methoxymethyl)pyrrolidin-1-yl (S)-N14 (2R/S)-2-(methoxymethyl)pyrrolidin-1-yl O1 oxetan-2-yl O2 oxetan-3-yl O3 oxan-4-yl

Particularly preferred are the diaminotriazine compounds of formula (I), and likewise the diaminotriazine compounds of formula (I) according to embodiment groups (1), (2), (2a), (2b), (3), (4), (5), (6) and (6a), wherein

Ar and Q are defined above,

R¹ is hydrogen; and

R² is hydrogen.

Particularly preferred are the diaminotriazine compounds of formula (I), and likewise the diaminotriazine compounds of formula (I) according to embodiment groups (1), (2), (2a), (2b), wherein

R¹ is hydrogen;

R² is hydrogen; and

X is as defined for groups (1), (2), (2a) and (2b) of embodiments.

Particularly preferred are the diaminotriazine compounds of formula (I), and likewise the diaminotriazine compounds of formula (I) according to embodiment groups (1), (2), (3) and (3a), wherein

R¹ is hydrogen;

R² is hydrogen;

X is as defined for groups (1), (2), (2a) and (2b) of embodiments and

wherein

is represented by one of the following moieties A or B

wherein

-   Ar, R^(a), Q are as defined above and wherein R^(b1), R^(b2) and     R^(b3) are identical or different and are hydrogen or have one of     the meanings of R^(b), wherein -   R^(b) is selected from the group consisting of halogen, CN,     C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,     C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, where the aliphatic parts of the     6 aforementioned radicals are unsubstituted, partly or completely     halogenated and     for q=2 or 3 it being possible that R^(b) are identical or     different.     More particular -   R^(b) is selected halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,     C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,     C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy, for q=2 or 3 it being possible     that R^(b) are identical or different.     Even more particular -   R^(b) is selected F, Cl, Br, methyl. -   R^(a) is selected from the group consisting of halogen, CN,     C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,     C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, where the aliphatic parts of the     6 aforementioned radicals are unsubstituted, partly or completely     halogenated and     for q=2 or 3 it being possible that R^(b) are identical or     different.     More particular -   R^(a) is selected halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,     C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,     C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy.     Even more particular     R^(a) is selected F, Cl, Br, CN or methyl.     More particular Q, A, R^(b) and R^(a) has the meanings as defined     above and     R^(b1) is selected from the group consisting of and hydrogen and     fluorine;     R^(b2) is selected from the group consisting of and hydrogen and     fluorine;     R^(b3) is selected from the group consisting of and hydrogen and     fluorine.

Especially preferred examples of the moiety Ar-Q is selected from the group consisting of phenyl, 4-methoxyphenyl, 4-cyanophenyl, 3-methylphenyl, 3,5-dimethylphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,5-dibromophenyl, 3,5-dimethoxyphenyl, 3,5-diethoxyphenyl, 3,5-Bis-(trifluoromethoxy)phenyl, 3,5-Bis-(trifluoromethyl)phenyl, 3,5-dicyanophenyl, 3-fluoro-5-methylphenyl, 3-chloro-5-methylphenyl, 3-bromo-5-methylphenyl, 3-methoxy-5-methylphenyl, 3-ethoxy-5-methylphenyl, 3-(trifluoromethoxy)-5-methylphenyl, 3-(trifluoromethyl)-5-methylphenyl, 3-(tert.-butyl)-5-methylphenyl, 3-cyano-5-methylphenyl, 3-chloro-5-fluorophenyl, 3-bromo-5-fluorophenyl, 3-fluoro-5-methoxyphenyl, 3-fluoro-5-ethoxyphenyl, 3-fluoro-5-(trifluoromethoxy)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 3-fluoro-5-(tert-butyl)phenyl, 3-fluoro-5-cyanophenyl, 3-chloro-5-methoxyphenyl, 3-chloro-5-ethoxyphenyl, 3-chloro-5-(trifluoromethoxy)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-chloro-5-(tert-butyl)phenyl, 3-chloro-5-cyanophenyl, 3-bromo-5-methoxyphenyl, 3-bromo-5-ethoxyphenyl, 3-bromo-5-(trifluoromethoxy)phenyl, 3-bromo-5-(trifluoromethyl)phenyl, 3-bromo-5-(tert-butyl)phenyl, 3-bromo-5-cyanophenyl, 3-ethoxy-5-methoxyphenyl, 3-(trifluoromethoxy)-5-methoxyphenyl, 3-methoxy-5-(trifluoromethyl)phenyl, 5-cyano-3-methoxyphenyl, 5-(tert-butyl)-3-methoxyphenyl, 3-(trifluoromethoxy)-5-ethoxyphenyl, 3-ethoxy-5-(trifluoromethyl)phenyl, 5-cyano-3-ethoxyphenyl, 5-(tert-butyl)-3-ethoxyphenyl, 3-(trifluoromethoxy)-5-(trifluoromethyl)phenyl, 3-(trifluoromethoxy)-5-(tert.-butyl)phenyl, 3-(trifluoromethoxy)-5-cyanophenyl, 3-(trifluoromethyl)-5-(tert.-butyl)phenyl, 3-(trifluoromethyl)-5-cyanophenyl, 3-cyano-5-(tert.-butyl)phenyl, 3,5-bis(tert.-butyl)phenyl, 3,5-bis(trifluoromethyl)phenoxy, 3-fluoro-5-(trifluoromethyl)phenoxy, 3-chloro-5-fluoro-phenoxy, 3,5-bis(bromo)phenoxy, 3-bromo-5-fluoro-phenoxy, 3-chloro-5-(methoxy)phenoxy, 3-chloro-5-bromo-phenoxy, 3-fluoro-5-cyano-phenoxy, 3-bromo-5-trifluormethoxy-phenoxy, 3-bromo-5-methoxy-phenoxy, 3-fluoro-5-methoxy-phenoxy, 3-methyl-5-methoxy-phenoxy, 3-chloro-5-trifluormethoxy-phenoxy, 3-trifluormethoxy-5-trifluomethyl-phenoxy, 3-methyl-5-trifluormethyl-phenoxy, 3-iodo-5-iodo-phenoxy, 3-ethoxy-5-ethoxy-phenoxy, 3-methyl-5-propoxy-phenoxy, 3-bromo-5-isopropoxy-phenoxy, 3-methyl-5-ethoxy-phenoxy, 3-methyl-5-(prop-2-ynoxy)-phenoxy, 3-bromo-5-trifluormethyl-phenoxy, 3-chloro-5-trifluormethyl-phenoxy, 3-methyl-5-(2-ethoxyethoxy)-phenoxy, 3-methyl-5-allyloxy-phenoxy, 3-methyl-5-methyl-phenoxy, 3-methyl-5-isobutoxy-phenoxy, 3-methyl-5-(2,2-difluoroethoxy)-phenoxy, 3-methyl-5-dimethylamino-phenoxy, 3-methyl-5-(2,2,2-trifluoroethoxy)-phenoxy, 3-fluoro-5-difluoromethoxy-phenoxy, 3-methyl-5-(cyclobutylmethoxy)-phenoxy, 3-iodo-5-methoxy-phenoxy, 3-methyl-5-cyclopentoxy-phenoxy, 3-methyl-5-cyclohexoxy-phenoxy, 3-trifluoromethyl-5-phenyl-phenoxy, 3-trifluoromethyl-phenoxy, 3-isopropoxy-phenoxy, 3-ethyl-phenoxy, 3-methoxycarbonyl-phenoxy, 3-tert-butyl-phenoxy, 3-bromo-phenoxy, 3-chloro-phenoxy, 3-difluoromethoxy-phenoxy, 3-iodo-5-methoxy-phenoxy, 3-trifluormethoxy-phenoxy, 3-difluoromethoxy-5-phenyl-phenoxy, 3-isopropoxy-5-fluoro-phenoxy, 3-iodo-5-fluoro-phenoxy, N-methyl-N-phenyl-amine and N-methyl-N-(m-tolyl)-amine, 3-methyl-phenoxy, 3-fluoro-phenoxy, 3-chloro-5-chloro-phenoxy, 3,5-dimethyl-4-chloro-phenoxy, 3,4-dimethyl-phenoxy, 2,4-dimethyl-phenoxy, 2-methyl-phenoxy, 3-flouro-5-fluoro-phenoxy, phenoxy, 2,3-dimethyl-phenoxy, 3,5-diethoxy-phenoxy, 3-methyl-5-chloro-phenoxy, 2,5-dimethyl-phenoxy, 2,6-dimethyl-phenoxy, 3-methoxy-phenyl, 4-methyl-phenyl, 4-methoxy-phenyl, 4-chloro-phenyl, 4-cyano-phenyl.

Particularly preferred is given to diaminotriazine compounds of formula (I.a), which corresponds to formula (I), wherein R¹ is hydrogen, R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are given in table A, and wherein X is as defined above and in particular X is selected from the group consisting of CF(CH₃)₂, CFCH₃CH₂CH₃, CHFCH₃, CHFCH₂CH₃, CF(CH₂CH₃)₂, CF₂CH₃, t-butyl, i-butyl, 2,2-dimethylpropyl, i-propyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl, 1-methylcyclobutyl, 1-methylcyclopentyl, C(CH₃)₂OCH₃, 1-methylcyclohexyl, 1-methoxyethyl, 1-methoxy-cyclopentyl, 1-methoxy-cyclobutyl, 1-methoxyl-cyclohexyl, 1-fluor-cyclopentyl, 1-fluor-cyclohexyl, 1-chlor-cyclopentyl, 1-chlor-cyclohexyl, 1-chlor-cyclobutyl, 2-methylpyrrolidin-1-yl, 2,2,2-trifluoroethoxy, azitidine, pyrrolidin-1-yl, 2-tetrahydrofuranyl, 2,4,6-tri-fluoro-phenyl, 2,6-difluoro-phenyl, 2-fluoro-phenyl or 1-cyclopropyl-1-fluoro-ethyl.

Examples of these compounds are those given in table A-1 to A-36. Particular preference is given to diaminotriazine compounds of formula (I.a), which corresponds to diaminotriazines of formula (I) wherein R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined in table A.

Table A-1: Compounds of formula (I.a), where X is CFCH₃CH₂CH₃, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-2: Compounds of formula (I.a), where X is CF(CH₃)₂, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-3: Compounds of formula (I.a), where X is CHFCH₃, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-4: Compounds of formula (I.a), where X is CHFCH₂CH₃, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-5: Compounds of formula (I.a), where X is CF(CH₂CH₃)₂ R¹ and R² is hydrogen Q is O, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-6: Compounds of formula (I.a), where X is CF₂CH₃ R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-7: Compounds of formula (I.a), where X is t-butyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ defined the rows of table A.

Table A-8: Compounds of formula (I.a), where X is i-butyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-9: Compounds of formula (I.a), where X is 2,2-dimethylpropyl R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-10: Compounds of formula (I.a), where X is i-propyl R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-11: Compounds of formula (I.a), where X is cyclobutyl, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-12: Compounds of formula (I.a), where X is cyclopentyl, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-13: Compounds of formula (I.a), where X is cyclohexyl, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-14: Compounds of formula (I.a), where X is 1-cyclopropylethyl, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-15: Compounds of formula (I.a), where X is 1-methylcyclobutyl, R¹ and R² is hydrogen Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-16: Compounds of formula (I.a), where X is 1-methylcyclopentyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-17: Compounds of formula (I.a), where X is C(CH₃)₂OCH₃, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-18: Compounds of formula (I.a), where X is 1-methylcyclohexyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-19: Compounds of formula (I.a), where X is 1-methoxyethyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-20: Compounds of formula (I.a), where X is 1-methoxy-cyclopentyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-21: Compounds of formula (I.a), where X is 1-methoxy-cyclobutyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-22: Compounds of formula (I.a), where X is 1-methoxyl-cyclohexyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-23: Compounds of formula (I.a), where X is 1-fluor-cyclopentyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-24: Compounds of formula (I.a), where X is 1-fluor-cyclohexyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-25: Compounds of formula (I.a), where X is 1-chlor-cyclopentyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-26: Compounds of formula (I.a), where X is 1-chlor-cyclohexyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-27: Compounds of formula (I.a), where X is 1-chlor-cyclobutyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-28: Compounds of formula (I.a), where X is 2-methylpyrrolidin-1-yl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-29: Compounds of formula (I.a), where X is 2,2,2-trifluoroethoxy, R¹ and R² is hydrogen, Q is O and R^(b1), R^(b2), R^(b3), R^(A1), R^(A2), Y¹ and Y² are defined the rows of table A.

Table A-30: Compounds of formula (I.a), where X is azitidine, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-31: Compounds of formula (I.a), where X is pyrrolidin-1-yl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-32: Compounds of formula (I.a), where X is 2-tetrahydrofuranyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-33: Compounds of formula (I.a), where X is 2,4,6-tri-fluoro-phenyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-34: Compounds of formula (I.a), where X is 2,6-difluoro-phenyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-35: Compounds of formula (I.a), where X is 2-fluoro-phenyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

Table A-36: Compounds of formula (I.a), where X is 1-cyclopropyl-1-fluoro-ethyl, R¹ and R² is hydrogen, Q is O and R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table A.

TABLE A no. R^(a) R^(b1) R^(b2) R^(b3) R⁶ R⁷ 1. F H H H CH₃ CH₃ 2. Cl H H H CH₃ CH₃ 3. CN H H H CH₃ CH₃ 4. F H F H CH₃ CH₃ 5. Cl H F H CH₃ CH₃ 6. CN H F H CH₃ CH₃ 7. F H Cl H CH₃ CH₃ 8. Cl H Cl H CH₃ CH₃ 9. CN H Cl H CH₃ CH₃ 10. F F F H CH₃ CH₃ 11. F H F F CH₃ CH₃ 12. F F H F CH₃ CH₃ 13. F F F F CH₃ CH₃ 14. F H H H CH₃ H 15. Cl H H H CH₃ H 16. CN H H H CH₃ H 17. F H F H CH₃ H 18. Cl H F H CH₃ H 19. CN H F H CH₃ H 20. F H Cl H CH₃ H 21. Cl H Cl H CH₃ H 22. CN H Cl H CH₃ H 23. F F F H CH₃ H 24. F H F F CH₃ H 25. F F H F CH₃ H 26. F F F F CH₃ H 27. F H H H CH₃ F 28. Cl H H H CH₃ F 29. CN H H H CH₃ F 30. F H F H CH₃ F 31. Cl H F H CH₃ F 32. CN H F H CH₃ F 33. F H Cl H CH₃ F 34. Cl H Cl H CH₃ F 35. CN H Cl H CH₃ F 36. F F F H CH₃ F 37. F H F F CH₃ F 38. F F H F CH₃ F 39. F F F F CH₃ F 40. F H H H CH₃ Cl 41. Cl H H H CH₃ Cl 42. CN H H H CH₃ Cl 43. F H F H CH₃ Cl 44. Cl H F H CH₃ Cl 45. CN H F H CH₃ Cl 46. F H Cl H CH₃ Cl 47. Cl H Cl H CH₃ Cl 48. CN H Cl H CH₃ Cl 49. F F F H CH₃ Cl 50. F H F F CH₃ Cl 51. F F H F CH₃ Cl 52. F F F F CH₃ Cl 53. F H H H CH₃ Br 54. Cl H H H CH₃ Br 55. CN H H H CH₃ Br 56. F H F H CH₃ Br 57. Cl H F H CH₃ Br 58. CN H F H CH₃ Br 59. F H Cl H CH₃ Br 60. Cl H Cl H CH₃ Br 61. CN H Cl H CH₃ Br 62. F F F H CH₃ Br 63. F H F F CH₃ Br 64. F F H F CH₃ Br 65. F F F F CH₃ Br 66. F H H H CH₃ OCH₃ 67. Cl H H H CH₃ OCH₃ 68. CN H H H CH₃ OCH₃ 69. F H F H CH₃ OCH₃ 70. Cl H F H CH₃ OCH₃ 71. CN H F H CH₃ OCH₃ 72. F H Cl H CH₃ OCH₃ 73. Cl H Cl H CH₃ OCH₃ 74. CN H Cl H CH₃ OCH₃ 75. F F F H CH₃ OCH₃ 76. F H F F CH₃ OCH₃ 77. F F H F CH₃ OCH₃ 78. F F F F CH₃ OCH₃ 79. F H H H CH₃ OCH₂CH₃ 80. Cl H H H CH₃ OCH₂CH₃ 81. CN H H H CH₃ OCH₂CH₃ 82. F H F H CH₃ OCH₂CH₃ 83. Cl H F H CH₃ OCH₂CH₃ 84. CN H F H CH₃ OCH₂CH₃ 85. F H Cl H CH₃ OCH₂CH₃ 86. Cl H Cl H CH₃ OCH₂CH₃ 87. CN H Cl H CH₃ OCH₂CH₃ 88. F F F H CH₃ OCH₂CH₃ 89. F H F F CH₃ OCH₂CH₃ 90. F F H F CH₃ OCH₂CH₃ 91. F F F F CH₃ OCH₂CH₃ 92. F H H H CH₃ OCF₃ 93. Cl H H H CH₃ OCF₃ 94. CN H H H CH₃ OCF₃ 95. F H F H CH₃ OCF₃ 96. Cl H F H CH₃ OCF₃ 97. CN H F H CH₃ OCF₃ 98. F H Cl H CH₃ OCF₃ 99. Cl H Cl H CH₃ OCF₃ 100. CN H Cl H CH₃ OCF₃ 101. F F F H CH₃ OCF₃ 102. F H F F CH₃ OCF₃ 103. F F H F CH₃ OCF₃ 104. F F F F CH₃ OCF₃ 105. F H H H CH₃ CF₃ 106. Cl H H H CH₃ CF₃ 107. CN H H H CH₃ CF₃ 108. F H F H CH₃ CF₃ 109. Cl H F H CH₃ CF₃ 110. CN H F H CH₃ CF₃ 111. F H Cl H CH₃ CF₃ 112. Cl H Cl H CH₃ CF₃ 113. CN H Cl H CH₃ CF₃ 114. F F F H CH₃ CF₃ 115. F H F F CH₃ CF₃ 116. F F H F CH₃ CF₃ 117. F F F F CH₃ CF₃ 118. F H H H CH₃ CN 119. Cl H H H CH₃ CN 120. CN H H H CH₃ CN 121. F H F H CH₃ CN 122. Cl H F H CH₃ CN 123. CN H F H CH₃ CN 124. F H Cl H CH₃ CN 125. Cl H Cl H CH₃ CN 126. CN H Cl H CH₃ CN 127. F F F H CH₃ CN 128. F H F F CH₃ CN 129. F F H F CH₃ CN 130. F F F F CH₃ CN 131. F H H H CH₃ tbutyl 132. Cl H H H CH₃ tbutyl 133. CN H H H CH₃ tbutyl 134. F H F H CH₃ tbutyl 135. Cl H F H CH₃ tbutyl 136. CN H F H CH₃ tbutyl 137. F H Cl H CH₃ tbutyl 138. Cl H Cl H CH₃ tbutyl 139. CN H Cl H CH₃ tbutyl 140. F F F H CH₃ tbutyl 141. F H F F CH₃ tbutyl 142. F F H F CH₃ tbutyl 143. F F F F CH₃ tbutyl 144. F H H H F F 145. Cl H H H F F 146. CN H H H F F 147. F H F H F F 148. Cl H F H F F 149. CN H F H F F 150. F H Cl H F F 151. Cl H Cl H F F 152. CN H Cl H F F 153. F F F H F F 154. F H F F F F 155. F F H F F F 156. F F F F F F 157. F H H H F Cl 158. Cl H H H F Cl 159. CN H H H F Cl 160. F H F H F Cl 161. Cl H F H F Cl 162. CN H F H F Cl 163. F H Cl H F Cl 164. Cl H Cl H F Cl 165. CN H Cl H F Cl 166. F F F H F Cl 167. F H F F F Cl 168. F F H F F Cl 169. F F F F F Cl 170. F H H H F Br 171. Cl H H H F Br 172. CN H H H F Br 173. F H F H F Br 174. Cl H F H F Br 175. CN H F H F Br 176. F H Cl H F Br 177. Cl H Cl H F Br 178. CN H Cl H F Br 179. F F F H F Br 180. F H F F F Br 181. F F H F F Br 182. F F F F F Br 183. F H H H F OCH₃ 184. Cl H H H F OCH₃ 185. CN H H H F OCH₃ 186. F H F H F OCH₃ 187. Cl H F H F OCH₃ 188. CN H F H F OCH₃ 189. F H Cl H F OCH₃ 190. Cl H Cl H F OCH₃ 191. CN H Cl H F OCH₃ 192. F F F H F OCH₃ 193. F H F F F OCH₃ 194. F F H F F OCH₃ 195. F F F F F OCH₃ 196. F H H H F OCH₂CH₃ 197. Cl H H H F OCH₂CH₃ 198. CN H H H F OCH₂CH₃ 199. F H F H F OCH₂CH₃ 200. Cl H F H F OCH₂CH₃ 201. CN H F H F OCH₂CH₃ 202. F H Cl H F OCH₂CH₃ 203. Cl H Cl H F OCH₂CH₃ 204. CN H Cl H F OCH₂CH₃ 205. F F F H F OCH₂CH₃ 206. F H F F F OCH₂CH₃ 207. F F H F F OCH₂CH₃ 208. F F F F F OCH₂CH₃ 209. F H H H F OCF₃ 210. Cl H H H F OCF₃ 211. CN H H H F OCF₃ 212. F H F H F OCF₃ 213. Cl H F H F OCF₃ 214. CN H F H F OCF₃ 215. F H Cl H F OCF₃ 216. Cl H Cl H F OCF₃ 217. CN H Cl H F OCF₃ 218. F F F H F OCF₃ 219. F H F F F OCF₃ 220. F F H F F OCF₃ 221. F F F F F OCF₃ 222. F H H H F CF₃ 223. Cl H H H F CF₃ 224. CN H H H F CF₃ 225. F H F H F CF₃ 226. Cl H F H F CF₃ 227. CN H F H F CF₃ 228. F H Cl H F CF₃ 229. Cl H Cl H F CF₃ 230. CN H Cl H F CF₃ 231. F F F H F CF₃ 232. F H F F F CF₃ 233. F F H F F CF₃ 234. F F F F F CF₃ 235. F H H H F CN 236. Cl H H H F CN 237. CN H H H F CN 238. F H F H F CN 239. Cl H F H F CN 240. CN H F H F CN 241. F H Cl H F CN 242. Cl H Cl H F CN 243. CN H Cl H F CN 244. F F F H F CN 245. F H F F F CN 246. F F H F F CN 247. F F F F F CN 248. F H H H F tbutyl 249. Cl H H H F tbutyl 250. CN H H H F tbutyl 251. F H F H F tbutyl 252. Cl H F H F tbutyl 253. CN H F H F tbutyl 254. F H Cl H F t butyl 255. Cl H Cl H F tbutyl 256. CN H Cl H F tbutyl 257. F F F H F tbutyl 258. F H F F F tbutyl 259. F F H F F tbutyl 260. F F F F F tbutyl 261. F H H H Cl Cl 262. Cl H H H Cl Cl 263. CN H H H Cl Cl 264. F H F H Cl Cl 265. Cl H F H Cl Cl 266. CN H F H Cl Cl 267. F H Cl H Cl Cl 268. Cl H Cl H Cl Cl 269. CN H Cl H Cl Cl 270. F F F H Cl Cl 271. F H F F Cl Cl 272. F F H F Cl Cl 273. F F F F Cl Cl 274. F H H H Cl Br 275. Cl H H H Cl Br 276. CN H H H Cl Br 277. F H F H Cl Br 278. Cl H F H Cl Br 279. CN H F H Cl Br 280. F H Cl H Cl Br 281. Cl H Cl H Cl Br 282. CN H Cl H Cl Br 283. F F F H Cl Br 284. F H F F Cl Br 285. F F H F Cl Br 286. F F F F Cl Br 287. F H H H Cl OCH₃ 288. Cl H H H Cl OCH₃ 289. CN H H H Cl OCH₃ 290. F H F H Cl OCH₃ 291. Cl H F H Cl OCH₃ 292. CN H F H Cl OCH₃ 293. F H Cl H Cl OCH₃ 294. Cl H Cl H Cl OCH₃ 295. CN H Cl H Cl OCH₃ 296. F F F H Cl OCH₃ 297. F H F F Cl OCH₃ 298. F F H F Cl OCH₃ 299. F F F F Cl OCH₃ 300. F H H H Cl OCH₂CH₃ 301. Cl H H H Cl OCH₂CH₃ 302. CN H H H Cl OCH₂CH₃ 303. F H F H Cl OCH₂CH₃ 304. Cl H F H Cl OCH₂CH₃ 305. CN H F H Cl OCH₂CH₃ 306. F H Cl H Cl OCH₂CH₃ 307. Cl H Cl H Cl OCH₂CH₃ 308. CN H Cl H Cl OCH₂CH₃ 309. F F F H Cl OCH₂CH₃ 310. F H F F Cl OCH₂CH₃ 311. F F H F Cl OCH₂CH₃ 312. F F F F Cl OCH₂CH₃ 313. F H H H Cl OCF₃ 314. Cl H H H Cl OCF₃ 315. CN H H H Cl OCF₃ 316. F H F H Cl OCF₃ 317. Cl H F H Cl OCF₃ 318. CN H F H Cl OCF₃ 319. F H Cl H Cl OCF₃ 320. Cl H Cl H Cl OCF₃ 321. CN H Cl H Cl OCF₃ 322. F F F H Cl OCF₃ 323. F H F F Cl OCF₃ 324. F F H F Cl OCF₃ 325. F F F F Cl OCF₃ 326. F H H H Cl CF₃ 327. Cl H H H Cl CF₃ 328. CN H H H Cl CF₃ 329. F H F H Cl CF₃ 330. Cl H F H Cl CF₃ 331. CN H F H Cl CF₃ 332. F H Cl H Cl CF₃ 333. Cl H Cl H Cl CF₃ 334. CN H Cl H Cl CF₃ 335. F F F H Cl CF₃ 336. F H F F Cl CF₃ 337. F F H F Cl CF₃ 338. F F F F Cl CF₃ 339. F H H H Cl CN 340. Cl H H H Cl CN 341. CN H H H Cl CN 342. F H F H Cl CN 343. Cl H F H Cl CN 344. CN H F H Cl CN 345. F H Cl H Cl CN 346. Cl H Cl H Cl CN 347. CN H Cl H Cl CN 348. F F F H Cl CN 349. F H F F Cl CN 350. F F H F Cl CN 351. F F F F Cl CN 352. F H H H Cl tbutyl 353. Cl H H H Cl tbutyl 354. CN H H H Cl tbutyl 355. F H F H Cl tbutyl 356. Cl H F H Cl tbutyl 357. CN H F H Cl tbutyl 358. F H Cl H Cl tbutyl 359. Cl H Cl H Cl tbutyl 360. CN H Cl H Cl tbutyl 361. F F F H Cl tbutyl 362. F H F F Cl tbutyl 363. F F H F Cl tbutyl 364. F F F F Cl tbutyl 365. F H H H Br Br 366. Cl H H H Br Br 367. CN H H H Br Br 368. F H F H Br Br 369. Cl H F H Br Br 370. CN H F H Br Br 371. F H Cl H Br Br 372. Cl H Cl H Br Br 373. CN H Cl H Br Br 374. F F F H Br Br 375. F H F F Br Br 376. F F H F Br Br 377. F F F F Br Br 378. F H H H Br OCH₃ 379. Cl H H H Br OCH₃ 380. CN H H H Br OCH₃ 381. F H F H Br OCH₃ 382. Cl H F H Br OCH₃ 383. CN H F H Br OCH₃ 384. F H Cl H Br OCH₃ 385. Cl H Cl H Br OCH₃ 386. CN H Cl H Br OCH₃ 387. F F F H Br OCH₃ 388. F H F F Br OCH₃ 389. F F H F Br OCH₃ 390. F F F F Br OCH₃ 391. F H H H Br OCH₂CH₃ 392. Cl H H H Br OCH₂CH₃ 393. CN H H H Br OCH₂CH₃ 394. F H F H Br OCH₂CH₃ 395. Cl H F H Br OCH₂CH₃ 396. CN H F H Br OCH₂CH₃ 397. F H Cl H Br OCH₂CH₃ 398. Cl H Cl H Br OCH₂CH₃ 399. CN H Cl H Br OCH₂CH₃ 400. F F F H Br OCH₂CH₃ 401. F H F F Br OCH₂CH₃ 402. F F H F Br OCH₂CH₃ 403. F F F F Br OCH₂CH₃ 404. F H H H Br OCF₃ 405. Cl H H H Br OCF₃ 406. CN H H H Br OCF₃ 407. F H F H Br OCF₃ 408. Cl H F H Br OCF₃ 409. CN H F H Br OCF₃ 410. F H Cl H Br OCF₃ 411. Cl H Cl H Br OCF₃ 412. CN H Cl H Br OCF₃ 413. F F F H Br OCF₃ 414. F H F F Br OCF₃ 415. F F H F Br OCF₃ 416. F F F F Br OCF₃ 417. F H H H Br CF₃ 418. Cl H H H Br CF₃ 419. CN H H H Br CF₃ 420. F H F H Br CF₃ 421. Cl H F H Br CF₃ 422. CN H F H Br CF₃ 423. F H Cl H Br CF₃ 424. Cl H Cl H Br CF₃ 425. CN H Cl H Br CF₃ 426. F F F H Br CF₃ 427. F H F F Br CF₃ 428. F F H F Br CF₃ 429. F F F F Br CF₃ 430. F H H H Br CN 431. Cl H H H Br CN 432. CN H H H Br CN 433. F H F H Br CN 434. Cl H F H Br CN 435. CN H F H Br CN 436. F H Cl H Br CN 437. Cl H Cl H Br CN 438. CN H Cl H Br CN 439. F F F H Br CN 440. F H F F Br CN 441. F F H F Br CN 442. F F F F Br CN 443. F H H H Br tbutyl 444. Cl H H H Br tbutyl 445. CN H H H Br tbutyl 446. F H F H Br tbutyl 447. Cl H F H Br tbutyl 448. CN H F H Br tbutyl 449. F H Cl H Br tbutyl 450. Cl H Cl H Br tbutyl 451. CN H Cl H Br tbutyl 452. F F F H Br tbutyl 453. F H F F Br tbutyl 454. F F H F Br tbutyl 455. F F F F Br tbutyl 456. F H H H OCH₃ OCH₃ 457. Cl H H H OCH₃ OCH₃ 458. CN H H H OCH₃ OCH₃ 459. F H F H OCH₃ OCH₃ 460. Cl H F H OCH₃ OCH₃ 461. CN H F H OCH₃ OCH₃ 462. F H Cl H OCH₃ OCH₃ 463. Cl H Cl H OCH₃ OCH₃ 464. CN H Cl H OCH₃ OCH₃ 465. F F F H OCH₃ OCH₃ 466. F H F F OCH₃ OCH₃ 467. F F H F OCH₃ OCH₃ 468. F F F F OCH₃ OCH₃ 469. F H H H OCH₃ OCH₂CH₃ 470. Cl H H H OCH₃ OCH₂CH₃ 471. CN H H H OCH₃ OCH₂CH₃ 472. F H F H OCH₃ OCH₂CH₃ 473. Cl H F H OCH₃ OCH₂CH₃ 474. CN H F H OCH₃ OCH₂CH₃ 475. F H Cl H OCH₃ OCH₂CH₃ 476. Cl H Cl H OCH₃ OCH₂CH₃ 477. CN H Cl H OCH₃ OCH₂CH₃ 478. F F F H OCH₃ OCH₂CH₃ 479. F H F F OCH₃ OCH₂CH₃ 480. F F H F OCH₃ OCH₂CH₃ 481. F F F F OCH₃ OCH₂CH₃ 482. F H H H OCH₃ OCF₃ 483. Cl H H H OCH₃ OCF₃ 484. CN H H H OCH₃ OCF₃ 485. F H F H OCH₃ OCF₃ 486. Cl H F H OCH₃ OCF₃ 487. CN H F H OCH₃ OCF₃ 488. F H Cl H OCH₃ OCF₃ 489. Cl H Cl H OCH₃ OCF₃ 490. CN H Cl H OCH₃ OCF₃ 491. F F F H OCH₃ OCF₃ 492. F H F F OCH₃ OCF₃ 493. F F H F OCH₃ OCF₃ 494. F F F F OCH₃ OCF₃ 495. F H H H OCH₃ CF₃ 496. Cl H H H OCH₃ CF₃ 497. CN H H H OCH₃ CF₃ 498. F H F H OCH₃ CF₃ 499. Cl H F H OCH₃ CF₃ 500. CN H F H OCH₃ CF₃ 501. F H Cl H OCH₃ CF₃ 502. Cl H Cl H OCH₃ CF₃ 503. CN H Cl H OCH₃ CF₃ 504. F F F H OCH₃ CF₃ 505. F H F F OCH₃ CF₃ 506. F F H F OCH₃ CF₃ 507. F F F F OCH₃ CF₃ 508. F H H H OCH₃ CN 509. Cl H H H OCH₃ CN 510. CN H H H OCH₃ CN 511. F H F H OCH₃ CN 512. Cl H F H OCH₃ CN 513. CN H F H OCH₃ CN 514. F H Cl H OCH₃ CN 515. Cl H Cl H OCH₃ CN 516. CN H Cl H OCH₃ CN 517. F F F H OCH₃ CN 518. F H F F OCH₃ CN 519. F F H F OCH₃ CN 520. F F F F OCH₃ CN 521. F H H H OCH₃ tbutyl 522. Cl H H H OCH₃ tbutyl 523. CN H H H OCH₃ tbutyl 524. F H F H OCH₃ tbutyl 525. Cl H F H OCH₃ tbutyl 526. CN H F H OCH₃ tbutyl 527. F H Cl H OCH₃ tbutyl 528. Cl H Cl H OCH₃ tbutyl 529. CN H Cl H OCH₃ tbutyl 530. F F F H OCH₃ tbutyl 531. F H F F OCH₃ tbutyl 532. F F H F OCH₃ tbutyl 533. F F F F OCH₃ tbutyl 534. F H H H OCH₂CH₃ OCH₂CH₃ 535. Cl H H H OCH₂CH₃ OCH₂CH₃ 536. CN H H H OCH₂CH₃ OCH₂CH₃ 537. F H F H OCH₂CH₃ OCH₂CH₃ 538. Cl H F H OCH₂CH₃ OCH₂CH₃ 539. CN H F H OCH₂CH₃ OCH₂CH₃ 540. F H Cl H OCH₂CH₃ OCH₂CH₃ 541. Cl H Cl H OCH₂CH₃ OCH₂CH₃ 542. CN H Cl H OCH₂CH₃ OCH₂CH₃ 543. F F F H OCH₂CH₃ OCH₂CH₃ 544. F H F F OCH₂CH₃ OCH₂CH₃ 545. F F H F OCH₂CH₃ OCH₂CH₃ 546. F F F F OCH₂CH₃ OCH₂CH₃ 547. F H H H OCH₂CH₃ OCF₃ 548. Cl H H H OCH₂CH₃ OCF₃ 549. CN H H H OCH₂CH₃ OCF₃ 550. F H F H OCH₂CH₃ OCF₃ 551. Cl H F H OCH₂CH₃ OCF₃ 552. CN H F H OCH₂CH₃ OCF₃ 553. F H Cl H OCH₂CH₃ OCF₃ 554. Cl H Cl H OCH₂CH₃ OCF₃ 555. CN H Cl H OCH₂CH₃ OCF₃ 556. F F F H OCH₂CH₃ OCF₃ 557. F H F F OCH₂CH₃ OCF₃ 558. F F H F OCH₂CH₃ OCF₃ 559. F F F F OCH₂CH₃ OCF₃ 560. F H H H OCH₂CH₃ CF₃ 561. Cl H H H OCH₂CH₃ CF₃ 562. CN H H H OCH₂CH₃ CF₃ 563. F H F H OCH₂CH₃ CF₃ 564. Cl H F H OCH₂CH₃ CF₃ 565. CN H F H OCH₂CH₃ CF₃ 566. F H Cl H OCH₂CH₃ CF₃ 567. Cl H Cl H OCH₂CH₃ CF₃ 568. CN H Cl H OCH₂CH₃ CF₃ 569. F F F H OCH₂CH₃ CF₃ 570. F H F F OCH₂CH₃ CF₃ 571. F F H F OCH₂CH₃ CF₃ 572. F F F F OCH₂CH₃ CF₃ 573. F H H H OCH₂CH₃ CN 574. Cl H H H OCH₂CH₃ CN 575. CN H H H OCH₂CH₃ CN 576. F H F H OCH₂CH₃ CN 577. Cl H F H OCH₂CH₃ CN 578. CN H F H OCH₂CH₃ CN 579. F H Cl H OCH₂CH₃ CN 580. Cl H Cl H OCH₂CH₃ CN 581. CN H Cl H OCH₂CH₃ CN 582. F F F H OCH₂CH₃ CN 583. F H F F OCH₂CH₃ CN 584. F F H F OCH₂CH₃ CN 585. F F F F OCH₂CH₃ CN 586. F H H H OCH₂CH₃ tbutyl 587. Cl H H H OCH₂CH₃ tbutyl 588. CN H H H OCH₂CH₃ tbutyl 589. F H F H OCH₂CH₃ tbutyl 590. Cl H F H OCH₂CH₃ tbutyl 591. CN H F H OCH₂CH₃ tbutyl 592. F H Cl H OCH₂CH₃ tbutyl 593. Cl H Cl H OCH₂CH₃ tbutyl 594. CN H Cl H OCH₂CH₃ tbutyl 595. F F F H OCH₂CH₃ tbutyl 596. F H F F OCH₂CH₃ tbutyl 597. F F H F OCH₂CH₃ tbutyl 598. F F F F OCH₂CH₃ tbutyl 599. F H H H OCF₃ OCF₃ 600. Cl H H H OCF₃ OCF₃ 601. CN H H H OCF₃ OCF₃ 602. F H F H OCF₃ OCF₃ 603. Cl H F H OCF₃ OCF₃ 604. CN H F H OCF₃ OCF₃ 605. F H Cl H OCF₃ OCF₃ 606. Cl H Cl H OCF₃ OCF₃ 607. CN H Cl H OCF₃ OCF₃ 608. F F F H OCF₃ OCF₃ 609. F H F F OCF₃ OCF₃ 610. F F H F OCF₃ OCF₃ 611. F F F F OCF₃ OCF₃ 612. F H H H OCF₃ CF₃ 613. Cl H H H OCF₃ CF₃ 614. CN H H H OCF₃ CF₃ 615. F H F H OCF₃ CF₃ 616. Cl H F H OCF₃ CF₃ 617. CN H F H OCF₃ CF₃ 618. F H Cl H OCF₃ CF₃ 619. Cl H Cl H OCF₃ CF₃ 620. CN H Cl H OCF₃ CF₃ 621. F F F H OCF₃ CF₃ 622. F H F F OCF₃ CF₃ 623. F F H F OCF₃ CF₃ 624. F F F F OCF₃ CF₃ 625. F H H H OCF₃ CN 626. Cl H H H OCF₃ CN 627. CN H H H OCF₃ CN 628. F H F H OCF₃ CN 629. Cl H F H OCF₃ CN 630. CN H F H OCF₃ CN 631. F H Cl H OCF₃ CN 632. Cl H Cl H OCF₃ CN 633. CN H Cl H OCF₃ CN 634. F F F H OCF₃ CN 635. F H F F OCF₃ CN 636. F F H F OCF₃ CN 637. F F F F OCF₃ CN 638. F H H H OCF₃ tbutyl 639. Cl H H H OCF₃ tbutyl 640. CN H H H OCF₃ tbutyl 641. F H F H OCF₃ tbutyl 642. Cl H F H OCF₃ tbutyl 643. CN H F H OCF₃ tbutyl 644. F H Cl H OCF₃ tbutyl 645. Cl H Cl H OCF₃ tbutyl 646. CN H Cl H OCF₃ tbutyl 647. F F F H OCF₃ tbutyl 648. F H F F OCF₃ tbutyl 649. F F H F OCF₃ tbutyl 650. F H H H CF₃ CF₃ 651. Cl H H H CF₃ CF₃ 652. CN H H H CF₃ CF₃ 653. F H F H CF₃ CF₃ 654. Cl H F H CF₃ CF₃ 655. CN H F H CF₃ CF₃ 656. F H Cl H CF₃ CF₃ 657. Cl H Cl H CF₃ CF₃ 658. CN H Cl H CF₃ CF₃ 659. F F F H CF₃ CF₃ 660. F H F F CF₃ CF₃ 661. F F H F CF₃ CF₃ 662. F F F F CF₃ CF₃ 663. F H H H CF₃ CN 664. Cl H H H CF₃ CN 665. CN H H H CF₃ CN 666. F H F H CF₃ CN 667. Cl H F H CF₃ CN 668. CN H F H CF₃ CN 669. F H Cl H CF₃ CN 670. Cl H Cl H CF₃ CN 671. CN H Cl H CF₃ CN 672. F F F H CF₃ CN 673. F H F F CF₃ CN 674. F F H F CF₃ CN 675. F F F F CF₃ CN 676. F H H H CF₃ tbutyl 677. Cl H H H CF₃ tbutyl 678. CN H H H CF₃ tbutyl 679. F H F H CF₃ tbutyl 680. Cl H F H CF₃ tbutyl 681. CN H F H CF₃ tbutyl 682. F H Cl H CF₃ tbutyl 683. Cl H Cl H CF₃ tbutyl 684. CN H Cl H CF₃ tbutyl 685. F F F H CF₃ tbutyl 686. F H F F CF₃ tbutyl 687. F F H F CF₃ tbutyl 688. F F F F CF₃ tbutyl 689. F H H H CN CN 690. Cl H H H CN CN 691. CN H H H CN CN 692. F H F H CN CN 693. Cl H F H CN CN 694. CN H F H CN CN 695. F H Cl H CN CN 696. Cl H Cl H CN CN 697. CN H Cl H CN CN 698. F F F H CN CN 699. F H F F CN CN 700. F F H F CN CN 701. F F F F CN CN 702. F H H H CN tbutyl 703. Cl H H H CN tbutyl 704. CN H H H CN tbutyl 705. F H F H CN tbutyl 706. Cl H F H CN tbutyl 707. CN H F H CN tbutyl 708. F H Cl H CN tbutyl 709. Cl H Cl H CN tbutyl 710. CN H Cl H CN tbutyl 711. F F F H CN tbutyl 712. F H F F CN tbutyl 713. F F H F CN tbutyl 714. F F F F CN tbutyl 715. F H H H tbutyl tbutyl 716. Cl H H H tbutyl tbutyl 717. CN H H H tbutyl tbutyl 718. F H F H tbutyl tbutyl 719. Cl H F H tbutyl tbutyl 720. CN H F H tbutyl tbutyl 721. F H Cl H tbutyl tbutyl 722. Cl H Cl H tbutyl tbutyl 723. CN H Cl H tbutyl tbutyl 724. F F F H tbutyl tbutyl 725. F H F F tbutyl tbutyl 726. F F H F tbutyl tbutyl 727. F F F F tbutyl tbutyl In following table A1 the abbreviation used in table A are given.

TABLE A1 CH₂CH₂CH₃ propyl C(CH₃)₃ tbutyl CH(CH₃)₂CH₂ ibutyl

Likewise particularly preferred is given to diaminotriazine compounds of formula (I.b), which corresponds to formula (I), wherein R¹ is hydrogen, R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are given in table B, and wherein X is as defined above and in particular X is selected from the group consisting of CF(CH₃)₂, CFCH₃CH₂CH₃, CHFCH₃, CHFCH₂CH₃, CF(CH₂CH₃)₂, CF₂CH₃, t-butyl, i-butyl, 2,2-dimethylpropyl, i-propyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl, 1-methylcyclobutyl, 1-methylcyclopentyl, C(CH₃)₂OCH₃, 1-methylcyclohexyl, 1-methoxyethyl, 1-methoxy-cyclopentyl, 1-methoxy-cyclobutyl, 1-methoxyl-cyclohexyl, 1-fluor-cyclopentyl, 1-fluor-cyclohexyl, 1-chlor-cyclopentyl, 1-chlor-cyclohexyl, 1-chlor-cyclobutyl, 2-methylpyrrolidin-1-yl, 2,2,2-trifluoroethoxy, azitidine, pyrrolidin-1-yl, 2-tetrahydrofuranyl, 2,4,6-tri-fluoro-phenyl, 2,6-difluoro-phenyl, 2-fluoro-phenyl or 1-cyclopropyl-1-fluoro-ethyl.

Examples of these compounds are those given in table B-1 to B-36. Particular preference is given to diaminotriazine compounds of formula (I.b), which corresponds to diaminotriazines of formula (I) wherein R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined in table B.

Table B-1: Compounds of formula (I.b), where X is CFCH₃CH₂CH₃, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-2: Compounds of formula (I.b), where X is CF(CH₃)₂, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-3: Compounds of formula (I.b), where X is CHFCH₃, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-4: Compounds of formula (I.b), where X is CHFCH₂CH₃, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-5: Compounds of formula (I.b), where X is CF(CH₂CH₃)₂ R¹ and R² is hydrogen Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-6: Compounds of formula (I.b), where X is CF₂CH₃ R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-7: Compounds of formula (I.b), where X is t-butyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ defined the rows of table B.

Table B-8: Compounds of formula (I.b), where X is i-butyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-9: Compounds of formula (I.b), where X is 2,2-dimethylpropyl R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-10: Compounds of formula (I.b), where X is i-propyl R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-11: Compounds of formula (I.b), where X is cyclobutyl, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-12: Compounds of formula (I.b), where X is cyclopentyl, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-13: Compounds of formula (I.b), where X is cyclohexyl, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-14: Compounds of formula (I.b), where X is 1-cyclopropylethyl, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-15: Compounds of formula (I.b), where X is 1-methylcyclobutyl, R¹ and R² is hydrogen and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-16: Compounds of formula (I.b), where X is 1-methylcyclopentyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-17: Compounds of formula (I.b), where X is C(CH₃)₂OCH₃, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-18: Compounds of formula (I.b), where X is 1-methylcyclohexyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-19: Compounds of formula (I.b), where X is 1-methoxyethyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-20: Compounds of formula (I.b), where X is 1-methoxy-cyclopentyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-21: Compounds of formula (I.b), where X is 1-methoxy-cyclobutyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-22: Compounds of formula (I.b), where X is 1-methoxyl-cyclohexyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-23: Compounds of formula (I.b), where X is 1-fluor-cyclopentyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-24: Compounds of formula (I.b), where X is 1-fluor-cyclohexyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-25: Compounds of formula (I.b), where X is 1-chlor-cyclopentyl, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-26: Compounds of formula (I.b), where X is 1-chlor-cyclohexyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-27: Compounds of formula (I.b), where X is 1-chlor-cyclobutyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-28: Compounds of formula (I.b), where X is 2-methylpyrrolidin-1-yl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-29: Compounds of formula (I.b), where X is 2,2,2-trifluoroethoxy, R¹ and R² is hydrogen, and Q, R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-30: Compounds of formula (I.b), where X is azitidine, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-31: Compounds of formula (I.b), where X is pyrrolidin-1-yl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-32: Compounds of formula (I.b), where X is 2-tetrahydrofuranyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-33: Compounds of formula (I.b), where X is 2,4,6-tri-fluoro-phenyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-34: Compounds of formula (I.b), where X is 2,6-difluoro-phenyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-35: Compounds of formula (I.b), where X is 2-fluoro-phenyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

Table B-36: Compounds of formula (I.a), where X is 1-cyclopropyl-1-fluoro-ethyl, R¹ and R² is hydrogen, and Q, R^(a), R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table B.

TABLE B No. R^(a) R^(b1) R^(b2) R^(b3) Q R⁷ R⁶ B-1. F H H H O CF₃ CF₃ B-2. F H H H O F CF₃ B-3. F H H H O Cl F B-4. F H H H O Br Br B-5. F H H H O Br F B-6. F H H H O Cl OMe B-7. F H H H O Cl Br B-8. F H H H O F CN B-9. F H H H O Br OCF₃ B-10. F H H H O Br OMe B-11. F H H H O F OMe B-12. F H H H O Me OMe B-13. F H H H O Cl OCF₃ B-14. F H H H O OMe CF₃ B-15. F H H H O Me CF₃ B-16. F H H H O I I B-17. F H H H O OEt OEt B-18. F H H H O Me OPr B-19. F H H H O Br O^(i)Pr B-20. F H H H O Me OEt B-21. F H H H O Me Prop-2-ynoxy B-22. F H H H O Br CF₃ B-23. F H H H O Cl CF₃ B-24. F H H H O Me 2-Ethoxyethoxy B-25. F H H H O Me Allyloxy B-26. F H H H O Me isobutoxy B-27. F H H H O Me 2,2- difluoroethoxy B-28. F H H H O CF₃ dimethylamino B-29. F H H H O Me 2,2,2- trifluoroethoxy B-30. F H H H O F OCHF₂ B-31. F H H H O Me cyclo- butylmethoxy B-32. F H H H O I OMe B-33. F H H H O Me cyclopentoxy B-34. F H H H O Me cyclohexoxy B-35. F H H H O CF₃ Ph B-36. F H H H O CF₃ H B-37. F H H H O i-Pr H B-38. F H H H O Et H B-39. F H H H O methoxy- H carbonyl B-40. F H H H O t-Bu H B-41. F H H H O Br H B-42. F H H H O Cl H B-43. F H H H O OCHF₂ H B-44. F H H H O Me Me B-45. F H H H O OCF₃ H B-46. F H H H O OCF₃ Ph B-47. F H H H O Isopropoxy F B-48. CN H H H O Me Me B-49. F H H H O I F B-50. F H H H NMe H H B-51. F H H H NMe Me H B-52. F F H H O Me Me

Likewise particularly preferred is given to diaminotriazine compounds of formula (I.c), which corresponds to formula (I), wherein R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are given in table C, and wherein X is as defined above and in particular X is selected from the group consisting of CF(CH₃)₂, CFCH₃CH₂CH₃, CHFCH₃, CHFCH₂CH₃, CF(CH₂CH₃)₂, CF₂CH₃, t-butyl, i-butyl, 2,2-dimethylpropyl, i-propyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl, 1-methylcyclobutyl, 1-methylcyclopentyl, C(CH₃)₂OCH₃, 1-methylcyclohexyl, 1-methoxyethyl, 1-methoxy-cyclopentyl, 1-methoxy-cyclobutyl, 1-methoxyl-cyclohexyl, 1-fluor-cyclopentyl, 1-fluor-cyclohexyl, 1-chlor-cyclopentyl, 1-chlor-cyclohexyl, 1-chlor-cyclobutyl, 2-methylpyrrolidin-1-yl, 2,2,2-trifluoroethoxy, azitidine, pyrrolidin-1-yl, 2-tetrahydrofuranyl, 2,4,6-tri-fluoro-phenyl, 2,6-difluoro-phenyl, 2-fluoro-phenyl or 1-cyclopropyl-1-fluoro-ethyl.

Examples of these compounds are those given in table C-1 to C-36. Particular preference is given to diaminotriazine compounds of formula (I.c), which corresponds to diaminotriazines of formula (I) wherein R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined in table C.

Table C-1: Compounds of formula (I.c), where X is CFCH₃CH₂CH₃, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-2: Compounds of formula (I.c), where X is CF(CH₃)₂, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-3: Compounds of formula (I.c), where X is CHFCH₃, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-4: Compounds of formula (I.c), where X is CHFCH₂CH₃, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-5: Compounds of formula (I.c), where X is CF(CH₂CH₃)₂ R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-6: Compounds of formula (I.c), where X is CF₂CH₃ R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-7: Compounds of formula (I.c), where X is t-butyl R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-8: Compounds of formula (I.c), where X is i-butyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-9: Compounds of formula (I.c), where X is 2,2-dimethylpropyl R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-10: Compounds of formula (I.c), where X is i-propyl R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-11: Compounds of formula (I.c), where X is cyclobutyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-12: Compounds of formula (I.c), where X is cyclopentyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-13: Compounds of formula (I.c), where X is cyclohexyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-14: Compounds of formula (I.c), where X is 1-cyclopropylethyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-15: Compounds of formula (I.c), where X is 1-methylcyclobutyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-16: Compounds of formula (I.c), where X is 1-methylcyclopentyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-17: Compounds of formula (I.c), where X is C(CH₃)₂OCH₃, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-18: Compounds of formula (I.c), where X is 1-methylcyclohexyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-19: Compounds of formula (I.c), where X is 1-methoxyethyl R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-20: Compounds of formula (I.c), where X is 1-methoxy-cyclopentyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-21: Compounds of formula (I.c), where X is 1-methoxy-cyclobutyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-22: Compounds of formula (I.c), where X is 1-methoxyl-cyclohexyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-23: Compounds of formula (I.c), where X is 1-fluor-cyclopentyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-24: Compounds of formula (I.c), where X is 1-fluor-cyclohexyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-25: Compounds of formula (I.c), where X is 1-chlor-cyclopentyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-26: Compounds of formula (I.c), where X is 1-chlor-cyclohexyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-27: Compounds of formula (I.c), where X is 1-chlor-cyclobutyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-28: Compounds of formula (I.c), where X is 2-methylpyrrolidin-1-yl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-29: Compounds of formula (I.c), where X is 2,2,2-trifluoroethoxy, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-30: Compounds of formula (I.c), where X is azitidine, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-31: Compounds of formula (I.c), where X is pyrrolidin-1-yl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-32: Compounds of formula (I.c), where X is 2-tetrahydrofuranyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-33: Compounds of formula (I.c), where X is 2,4,6-tri-fluoro-phenyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-34: Compounds of formula (I.c), where X is 2,6-difluoro-phenyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-35: Compounds of formula (I.c), where X is 2-fluoro-phenyl, R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

Table C-36: Compounds of formula (I.a), where X is 1-cyclopropyl-1-fluoro-ethyl R^(a) is F, Q is O, and R¹, R² R^(b1), R^(b2), R^(b3), R⁶, R⁷ are defined the rows of table C.

TABLE C No. R¹ R² R^(b1) R^(b2) R^(b3) R⁷ R⁶ C-1. CH₃ H H H H CH₃ CH₃ C-2. H CH₃ H H H CH₃ CH₃ C-3. CH₃ CH₃ H H H CH₃ CH₃ C-4. C(═O)CH₃ H H H H CH₃ CH₃ C-5. H C(═O)CH₃ H H H CH₃ CH₃ C-6. C(═O)CH₃ C(═O)CH₃ H H H CH₃ CH₃ C-7. C(═O)CH₃ CH₃ H H H CH₃ CH₃ C-8. CH₃ C(═O)CH₃ H H H CH₃ CH₃

The diaminotriazine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes:

Process A)

The diaminotriazine compounds of formula (I), wherein R² is as defined above and in particular H, C₁-C₆-alkyl or (C₁-C₆-alkoxy)-C₁-C₆-alkyl, can be prepared by reacting halotriazines of formula (II) with amines of formula (III) in the presence of a base and a catalyst as depicted in the following scheme 1:

In scheme 1, the variable B is

# donates the bond to the remainder molecule,

variables R¹, R², Ar, R^(a), Q, R^(b), p, q and X have the above meanings while Hal is halogen, in particular bromine or chlorine and especially chlorine.

Compounds of formula (II) are novel and valuable intermediates in the production of the diaminotriazine compounds of formula (I) and therefore form part of the present invention.

Particular embodiments of the halotriazines of formula (II) relate to compounds, where the variables Hal, R¹, R² and X have in particular the following meanings:

-   Hal preferably Cl or Br, especially Cl; -   R² is in particular H, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl; more     particularly H, C₁-C₄-alkoxy-C₁-C₄-alkyl, such as CH₂OCH₃;     especially hydrogen; -   X is as defined above and in particular as defined in embodiments     groups.

Particular embodiments relate to the halotriazines of formula (II.a), which correspond to the halotriazines of formula (II) wherein R² is hydrogen and Hal is Cl. Further particular embodiments relate to the halotriazines of formula (II.b), which correspond to the halotriazines of formula (II) wherein R² is hydrogen and Hal is Br:

Particular examples of the compounds of formulae (II.a) and (II.b) are those, wherein X is as defined in the table A.

In formula (III)

-   R¹ is in particular H, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl;     -   more particularly H, (C₁-C₄-alkoxy)-C₁-C₄-alkyl, such as         CH₂OCH₃;     -   especially hydrogen; and -   B is as defined above.

The reaction of the halotriazines of formula (II) with the amines of formula (III) is usually carried out at temperatures in the range from 50° C. to the boiling point of the reaction mixture, preferably from 50° C. to 150° C., particularly preferably from 60° C. to 100° C., in an inert organic solvent (e.g. P. Dao et al., Tetrahedron 2012, 68, 3856-3860).

The reaction can be carried out at atmospheric pressure or under elevated pressure, if appropriate, under an inert gas, continuously or batchwise.

In one embodiment of the process according to the invention, the halotriazines of formula (II) and the amines of formula (III) are used in equimolar amounts.

In another embodiment of the process according to the invention, the amines of formula (III) are used in excess with regard to the halotriazines of formula (II).

Preferably the molar ratio of the amines of formula (III) to the halotriazines of formula (II) is in the range from 2:1 to 1:1, preferably 1.5:1 to 1:1, especially preferred 1.2:1.

The reaction of the halotriazines of formula (II) with the amines of formula (III) is usually carried out in an organic solvent. Suitable in principle are all solvents which are capable of dissolving the halotriazines of formula (II) and the amines of formula (II) at least partly and preferably fully under reaction conditions. Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N′-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP). Preferred solvents are ethers as defined above. The term solvent as used herein also includes mixtures of two or more of the above compounds.

The reaction of the halotriazines of formula (II) with the amines of formula (III) is usually carried out in the presence of a base. Examples of suitable bases include metal-containing bases and nitrogen-containing bases. Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal formates, acetates and other metal salts of carboxylic acids, such as sodium formate, sodium benzoate, lithium acetate, sodium acetate, potassium acetate, magnesium acetate, and calcium acetate; alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as sodium phosphate, potassium phosphate and calcium phosphate; alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium; and furthermore organic bases, such as tertiary amines such as tri-C₁-C₆-alkylamines, for example triethylamine, trimethylamine, N-ethyldiisopropylamine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and also bicyclic amines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN). Preferred bases are alkali metal and alkaline earth metal alkoxides as defined above. The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base. The bases can be used in excess, preferably from 1 to 10, especially preferred from 2 to 4 base equivalents based on the halotriazines of formula (II), and they may also be used as the solvent.

The reaction of the halotriazines of formula (II) with the amines of formula (III) may be carried out in the presence of a catalyst. Examples of suitable catalysts include for example, palladium based catalysts like, for example, Palladium(II)acetate, tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palladium(II)chloride or (1,1,-bis(diphenylphosphino)ferrocene)-dichloropalladium(II),

and optionally suitable additives such as, for example, phosphines like, for example, P(o-tolyl)₃, triphenylphosphine or BINAP (2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl). The amount of catalyst is usually 10 to 20 mol % (0.1 to 0.2 equivalents) based on the halotriazines of formula (II).

The end of the reaction can easily be determined by the skilled worker by means of routine methods.

The reaction mixtures are worked up in a customary manner, for example by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product.

The amines of formula (III) used for the preparation of diaminotriazine compounds of formula (I), wherein R¹ is H, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl or C₁-C₆-alkoxy, are commercially available and/or can be prepared by analogy to known literature.

The halotriazines of formula (III) required for the preparation of diaminotriazine compounds of formula (I), wherein R² is H, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl or C₁-C₆-alkoxy, can be prepared by analogy (e.g. J. K. Chakrabarti et al., Tetrahedron 1975, 31, 1879-1882) by reacting thiotriazines of formula (IV) with a halogen, as depicted in scheme 2:

The variable X in formulae (II) and (VI) has the meanings, in particular the preferred meanings, as defined above in context of formula (I).

-   R* is C₁-C₆-alkyl, C₂-C₆-haloalkyl or phenyl;     -   in particular C₁-C₄-alkyl or C₂-C₄-haloalkyl;     -   more particularly C₁-C₄-alkyl;     -   especially CH₃; and

Compounds of formula (IV) are novel and valuable intermediates in the production of the diaminotriazine compounds of formula (I) and therefore also form part of the present invention.

Particular embodiments of the compounds of formula (IV) relate to compounds, where the variables R*, R² and X have in particular the following meanings:

-   R* is C₁-C₆-alkyl, C₂-C₆-haloalkyl or phenyl;     -   in particular C₁-C₄-alkyl or C₂-C₄-haloalkyl;     -   more particularly C₁-C₄-alkyl;     -   especially CH₃; and -   R² is in particular H, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl;     -   more particularly H, (C₁-C₄-alkoxy)-C₁-C₄-alkyl, such as         CH₂OCH₃;     -   especially hydrogen; -   X is as defined above and in particular as defined in the     embodiments groups.

Particular embodiments relate to the compounds of formula (IV.a), which correspond to the compounds of formula (IV) wherein R² is hydrogen and R* is CH₃.

Particular examples of the compounds of formulae (IV.a) are those, wherein X is as defined in the table B above.

The reaction of the thiotriazines of formula (IV) with the halogen is usually carried out from 0° C. to the boiling point of the reaction mixture, preferably from 15° C. to the boiling point of the reaction mixture, particularly preferably from 15° C. to 40° C., in an inert organic solvent (e.g. J. K. Chakrabarti et al., Tetrahedron 1975, 31, 1879-1882).

The reaction can be carried out at atmospheric pressure or under elevated pressure, if appropriate under an inert gas, continuously or batchwise.

In the reaction of the thiotriazines of formula (IV) with, halogen is generally used in excess with regard to the thiotriazines of formula (IV).

The reaction of the thiotriazines of formula (IV) with the halogen is usually carried out in an organic solvent.

Suitable in principle are all solvents which are capable of dissolving the thiotriazines of formula (IV) and the halogen at least partly and preferably fully under reaction conditions. Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of C₅-C₈-alkanes, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform and carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol, as well as organic acids like formic acid, acetic acid, propionic acid, oxalic acid, citric acid, trifluoroacetic acid. Preferred solvents are halogenated hydrocarbons and organic acids as defined above. The term solvent as used herein also includes mixtures of two or more of the above compounds. The end of the reaction can easily be determined by the skilled worker by means of routine methods. The reaction mixtures are worked up in a customary manner, for example by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product.

The halotriazines of formula (II) required for the preparation of diaminotriazine compounds of formula (I), wherein R² is H, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, can also be prepared by reacting 2,4-dichlorotriazines of formula (VII) with a an amine H₂N—R², in particular with ammonia, as depicted in scheme 3:

The variable X in formulae (II) and (VII) has the meanings, in particular the preferred meanings, as defined above in context of formula (I).

Hal and Hal′ are each, independently, halogen, in particular bromine or chlorine, especially chlorine.

The reaction depicted in scheme 3 can be performed by simply mixing the required amounts of the compound of formula (VII) with the amine H₂N—R² or by analogy to the reaction depicted in step 1. Preferably the molar ratio of the amine to the halotriazines of formula (II) is in the range from 10:1 to 1:1, preferably 5:1 to 1:1.

Compound (IV) can be obtained by reaction of compound (II) with mercaptan R*—SH.

The reaction depicted in scheme 3 is preferably carried out in an inert solvent. Examples of suitable solvents are nitromethane, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N′-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP) and mixtures thereof with water or with aliphatic hydrocarbons such as pentane, hexane, cyclohexane or with mixtures of C₅-C₈-alkane. Preferred solvents are ethers as defined above and mixtures thereof with water. The term solvent as used herein also includes mixtures of two or more of the above compounds.

The reaction depicted in scheme 1 may be performed in the presence of an auxiliary base. Suitable bases are those mentioned in context with the reaction depicted in scheme 1. However, the amine H₂N—R² may itself serve as an auxiliary base. In this case, usually an excess of the amine H₂N—R² is used.

Process B)

The diaminotriazine compounds of formula (I), wherein

-   R² is different from hydrogen, e.g. C₁-C₆-alkyl,     (C₁-C₆-alkoxy)-C₁-C₆-alkyl, CN, (C₁-C₆-alkyl)carbonyl,     (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, phenylsulfonyl,     phenyl, phenyl-C₁-C₆ alkyl, phenylcarbonyl or phenoxycarbonyl,     -   wherein the phenyl is unsubstituted or substituted as defined         above for the respective radicals in formula (I);

can be prepared by reacting azines of formula (I), wherein R² is hydrogen with a compound of formula (V) as depicted in scheme 4:

The variable B is

# donates the bond to the remainder molecule,

variables R¹, Ar, R^(a), Q, R^(b), p, q and X have the meanings, in particular the preferred meanings, as in formula (I) mentioned above,

-   R² is different from hydrogen, e.g. C₁-C₆-alkyl,     (C₁-C₆-alkoxy)-C₁-C₆-alkyl, CN, (C₁-C₆-alkyl)carbonyl,     (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, phenylsulfonyl,     phenyl, phenyl-C₁-C₆ alkyl, phenylcarbonyl or phenoxycarbonyl,     -   wherein the phenyl is unsubstituted or substituted as defined         above for the respective radicals in formula (I);     -   in particular C₁-C₄-alkyl, CN, (C₁-C₆-alkyl)carbonyl,         (C₁-C₆-alkoxy)carbonyl or (C₁-C₆-alkyl)sulfonyl;     -   especially CN, COCH₃, COOCH₃ or SO₂CH₃; and -   Y is halogen or oxycarbonyl-C₁-C₆-alkyl;     -   in particular halogen;     -   especially Cl, I or Br.         Process C)

The diaminotriazine compounds of formula (I), wherein

-   R¹ is different from hydrogen, e.g. C₁-C₆-alkyl,     (C₁-C₆-alkoxy)-C₁-C₆-alkyl, CN, (C₁-C₆-alkyl)carbonyl,     (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, phenylsulfonyl,     phenyl, phenyl-C₁-C₆ alkyl, phenylcarbonyl or phenoxycarbonyl,     -   wherein the phenyl is unsubstituted or substituted by one to         five substituents selected from the group consisting of halogen,         CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkoxy;

can be prepared by reacting azines of formula (I), wherein R¹ is hydrogen with a compound of formula (VI), as depicted in scheme 5:

The variable B is

# donates the bond to the remainder molecule,

variables Ar, R^(a), Q, R^(b), p, q, R² and X have the meanings, in particular the preferred meanings, as in formula (I) mentioned above,

-   R¹ is different from hydrogen, e.g. C₁-C₆-alkyl,     (C₁-C₆-alkoxy)-C₁-C₆-alkyl, CN, (C₁-C₆-alkyl)carbonyl,     (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, phenylsulfonyl,     phenyl, phenyl-C₁-C₆ alkyl, phenylcarbonyl or phenoxycarbonyl,     -   wherein the phenyl is unsubstituted or substituted as defined         above for the respective radicals in formula (I);     -   in particular C₁-C₄-alkyl, CN, (C₁-C₆-alkyl)carbonyl,         (C₁-C₆-alkoxy)carbonyl or (C₁-C₆-alkyl)sulfonyl;     -   especially CN, COCH₃, COOCH₃ or SO₂CH₃; and -   V is halogen or oxycarbonyl-C₁-C₆-alkyl;     -   in particular halogen;     -   especially Cl, I or Br.         Both processes B and C independently of one another usually         carried out at from 0° C. to the boiling point of the reaction         mixture, preferably from 23° C. to 130° C., particularly         preferably from 23° C. to 100° C., (e.g. Y. Yuki et al.,         Polym. J. 1992, 24, 791-799).         Both processes B and C independently of one another can be         carried out at atmospheric pressure or under elevated pressure,         if appropriate under an inert gas, continuously or batchwise.         In one embodiment of processes B and C according to the         invention independently of one another, the diaminotriazine         compounds of formula (I), wherein R², or R¹ respectively, is         hydrogen are used in excess with regard to the compound of         formula (V), or (VI) respectively.         In another embodiment of processes B and C according to the         invention independently of one another, the diaminotriazine         compounds of formula (I), wherein R², or R¹ respectively, is         hydrogen and the compound of formula (V), or (VI) respectively,         are used in equimolar amounts.         Preferably the molar ratio of the diaminotriazine compounds of         formula (I), wherein R², or R¹ respectively, is hydrogen to the         compound of formula (V), or (VI) respectively is in the range         from 1:1.5 to 1:1, preferably 1:1.2 to 1:1, especially preferred         1:1.         Both processes B and C independently of one another are usually         carried out in an organic solvent. Suitable in principle are all         solvents which are capable of dissolving the diaminotriazine         compounds of formula (I), wherein R², or R¹ respectively, is         hydrogen and the compound of formula (V), or (VI) respectively,         at least partly and preferably fully under reaction conditions.         Examples of suitable solvents are halogenated hydrocarbons such         as dichloromethane, 1,2-dichloroethane, chloroform, carbon         tetrachloride and chlorobenzene; ethers such as diethyl ether,         diisopropyl ether, tert.-butyl methylether (TBME), dioxane,         anisole and tetrahydrofuran (THF); nitriles such as acetonitrile         and propionitrile; alcohols such as methanol, ethanol,         n-propanol, isopropanol, n-butanol and tert.-butanol; organic         acids like formic acid, acetic acid, propionic acid, oxalic         acid, methylbenzenesulfonic acid, benzenesulfonic acid,         camphorsulfonic acid, citric acid, trifluoroacetic acid as well         as dipolar aprotic solvents such as sulfolane,         dimethylsulfoxide, N,N-dimethylformamide (DMF),         N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone         (DMI), N,N′-dimethylpropylene urea (DMPU), dimethyl sulfoxide         (DMSO) and 1-methyl-2 pyrrolidinone (NMP). Preferred solvents         are halogenated hydrocarbons, ethers and dipolar aprotic         solvents as mentioned above. More preferred solvents are         dichloromethane or dioxane. It is also possible to use mixtures         of the solvents mentioned. The term solvent as used herein also         includes mixtures of two or more of the above compounds.         Both processes B and C independently of one another are         optionally carried out in the presence of a base. Examples of         suitable bases include metal-containing bases and         nitrogen-containing bases. Examples of suitable metal-containing         bases are inorganic compounds such as alkali metal and alkaline         earth metal hydrides such as lithium hydride, sodium hydride,         potassium hydride and calcium hydride, alkali metal and alkaline         earth metal carbonates such as lithium carbonate, sodium         carbonate, potassium carbonate, magnesium carbonate, and calcium         carbonate, as well as alkali metal hydrogen carbonates         (bicarbonates) such as lithium hydrogen carbonate, sodium         hydrogen carbonate, potassium hydrogen carbonate; alkali metal         and alkaline earth metal phosphates such as sodium phosphate,         potassium phosphate and calcium phosphate; and furthermore         organic bases, such as tertiary amines such as         tri-C₁-C₆-alkylamines, for example triethylamine,         trimethylamine, N-ethyldiisopropylamine, and N-methylpiperidine,         pyridine, substituted pyridines such as collidine, lutidine,         N-methylmorpholine and 4-dimethylaminopyridine (DMAP), and also         bicyclic amines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)         or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN). Preferred bases are         organic bases and alkali metal carbonates as mentioned above.         Especially preferred bases are organic bases as mentioned above.         The term base as used herein also includes mixtures of two or         more, preferably two of the above compounds. The bases are         generally employed in excess; however they can also be employed         in equimolar amounts, or, if appropriate, can be used as         solvent. Preferably from 1 to 5 base equivalents, particularly         preferred 3 base equivalents of base are used, based on the         diaminotriazine compounds of formula (I).         Work-up of the reaction mixture is performed by standard         procedures.         The compounds of formula (V), or (VI) respectively, are known         compounds. They are commercially available or can be prepared in         analogy to known methods.         Process D)         The diaminotriazine compounds of formula (I), wherein R¹ and R²         are defined above, can be prepared by reacting biguanidines of         formula (VII) with carbonyl compounds of formula (VIII) in the         presence of a base:

The variable B is

# donates the bond to the remainder molecule, variables R¹, R², Ar, R^(a), Q, R^(b), p, q and X have the meanings, in particular the preferred meanings, as in formula (I) mentioned above, and

-   L¹ is a nucleophilically displaceable leaving group such as halogen,     CN, C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyloxy or     C₁-C₆-alkoxycarbonyloxy;     -   preferably halogen or C₁-C₆-alkoxy;     -   particularly preferred Cl or C₁-C₆-alkoxy,     -   also particularly preferred halogen;     -   especially preferred Cl.

The reaction of biguanidines of formula (VII) with carbonyl compounds of formula (VIII) is usually carried out at temperatures from 50° C. to the boiling point of the reaction mixture, preferably from 50° C. to 200° C. (e.g. R. Sathunuru et al., J. Heterocycl. Chem. 2008, 45, 1673-1678).

The reaction can be carried out at atmospheric pressure or under elevated pressure, if appropriate under an inert gas, continuously or batchwise.

In one embodiment of the process according to the invention, the biguanidines of formula (VII) and the carbonyl compounds of formula (VIII) are used in equimolar amounts.

In another embodiment of the process according to the invention, the carbonyl compounds of formula (VIII) are used in excess with regard to the biguanidines of formula (VII).

Preferably the molar ratio of the carbonyl compounds of formula (VIII) to the biguanidines of formula (VII) is in the range from 1.5:1 to 1:1, preferably 1.2:1 to 1:1, especially preferred 1.2:1, also especially preferred 1:1.

The reaction of the biguanidines of formula (VII) with the carbonyl compounds of formula (VIII) is carried out in an organic solvent.

Suitable in principle are all solvents which are capable of dissolving the biguanidines of formula (VII) and the carbonyl compounds of formula (VIII) at least partly and preferably fully under reaction conditions.

Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C₅-C₈-alkanes; romatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N′-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).

Preferred solvents are ethers and dipolar aprotic solvents as defined above. More preferred solvents are ethers as defined above.

The term solvent as used herein also includes mixtures of two or more of the above compounds.

The reaction of the biguanidines of formula (VII) with the carbonyl compounds of formula (VIII) is carried out in the presence of a base.

Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as sodium phosphate, potassium phosphate and calcium phosphate; and furthermore organic bases, such as tertiary amines such as tri-C₁-C₆-alkylamines, for example triethylamine, trimethylamine, N-ethyldiisopropylamine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4-dimethylaminopyridine (DMAP), and also bicyclic amines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

Preferred bases are tri-C₁-C₆-alkylamines as defined above. The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base. The bases are generally employed in excess; however they can also be employed in equimolar amounts, or, if appropriate, can be used as solvent. Preferably from 1 to 5 base equivalents, particularly preferred 3 base equivalents of base are used, based on the biguanidines of formula (VII). The end of the reaction can easily be determined by the skilled worker by means of routine methods.

The reaction mixtures are worked up in a customary manner, for example by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product.

Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately elevated temperature.

If the intermediates and the end products are obtained as solid, purification can also be carried out by recrystallisation or digestion.

The carbonyl compounds of formula (VIII) required for the preparation of azines of formula (I) are known in the art or they can be prepared in accordance and/or are commercially available.

The biguanidines of formula (VII) required for the preparation of azines of formula (I), wherein R¹ and R² are defined above, can be prepared by reacting guanidines of formula (IX) with amines of formula (X) in the presence of an acid:

The variable B is

# donates the bond to the remainder molecule,

variables Ar, R^(a), Q, R^(b), p, q have the meanings, in particular the preferred meanings, as in formula (I) mentioned above.

The reaction of guanidines of formula (IX) with amines of formula (X) is usually carried out from 50° C. to 150° C., preferably from 80° C. to 130° C.

Microwave-Technology was used where applicable (e.g. C. O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry, Weinheim 2012).

The reaction can be carried out at atmospheric pressure or under elevated pressure, if appropriate under an inert gas, continuously or batchwise.

In one embodiment of the process according to the invention, the guanidines of formula (IX) and the amines of formula (X) are used in equimolar amounts.

In another embodiment of the process according to the invention, the amines of formula (X) are used in excess with regard to the guanidines of formula (IX).

Preferably the molar ratio of the amines of formula (X) to the guanidines of formula (IX) is in the range from 2:1 to 1:1, preferably 1.5:1 to 1:1, especially preferred 1:1.

The reaction of the guanidines of formula (IX) with the amines of formula (X) is carried out in an organic solvent.

Suitable in principle are all solvents which are capable of dissolving the guanidines of formula (IX) and the amines of formula (X) at least partly and preferably fully under reaction conditions.

Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N′-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).

Preferred solvents are ethers, nitriles and dipolar aprotic solvents as defined above.

More preferred solvents are nitriles as defined above.

The term solvent as used herein also includes mixtures of two or more of the above compounds.

The reaction of the guanidines of formula (IX) with the amines of formula (X) is carried out in the presence of an acid.

As acids and acidic catalysts inorganic acids like hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid; mineral acids like hydrochloric acid, sulfuric acid, phosphoric acid, Lewis acids like boron trifluoride, aluminium chloride, ferric-III-chloride, tin-IV-chloride, titanium-IV-chloride and zinc-II-chloride, as well as organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid, can be used.

The acids are generally employed in excess or, if appropriate, can be used as solvent.

Work up can be carried out in a known manner.

The guanidines of formula (IX) required for the preparation of biguanidines of formula (VII) are commercially available or can be prepared in accordance with literature procedures (e.g. J. L. LaMattina et al., J. Med. Chem. 1990, 33, 543-552; A. Perez-Medrano et al., J. Med. Chem. 2009, 52, 3366-3376).

The amines of formula (X) required for the preparation of biguanidines of formula (VII) are commercially available.

The compounds of formula (I) have herbicidal activity. Therefore, they can be used for controlling unwanted or undesired plants or vegetation. They can also be used in a method for controlling unwanted or undesired plants or vegetation, which method comprises allowing at least one compound of formula (I) or a salt thereof to act on plants, their environment or on seed. In order to allow the compound of formula (I) or a salt thereof to act on plants, their environment or on seed the compounds of the invention are applied to the plants, their environment or to the seed of said plants.

To widen the spectrum of action and to achieve synergistic effects, the diaminotriazine compounds of formula (I) may be mixed with a large number of representatives of other herbicidal or growth-regulating active ingredient groups and then applied concomitantly.

Suitable components for mixtures are, for example, herbicides from the classes of the acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoroamidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, ureas.

The invention also relates to combinations of diaminotriazine compounds of formula (I) with at least one further herbicide B and/or at least one safener C).

The further herbicidal compound B (component B) is in particular selected from the herbicides of class b1) to b15):

-   -   b1) lipid biosynthesis inhibitors;     -   b2) acetolactate synthase inhibitors (ALS inhibitors);     -   b3) photosynthesis inhibitors;     -   b4) protoporphyrinogen-IX oxidase inhibitors,     -   b5) bleacher herbicides;     -   b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP         inhibitors);     -   b7) glutamine synthetase inhibitors;     -   b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);     -   b9) mitosis inhibitors;     -   b10) inhibitors of the synthesis of very long chain fatty acids         (VLCFA inhibitors);     -   b11) cellulose biosynthesis inhibitors;     -   b12) decoupler herbicides;     -   b13) auxinic herbicides;     -   b14) auxin transport inhibitors; and     -   b15) other herbicides selected from the group consisting of         bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin,         cumyluron, dalapon, dazomet, difenzoquat,         difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and         its salts, etobenzanid, flamprop, flamprop-isopropyl,         flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl,         flurenol, flurenol-butyl, flurprimidol, fosamine,         fosamine-ammonium, indanofan, indaziflam, maleic hydrazide,         mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide,         methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid,         oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine,         triaziflam, tridiphane and         6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS         499223-49-3) and its salts and esters;

including their agriculturally acceptable salts or derivatives such as ethers, esters or amides.

-   -   In one embodiment of the present invention the compositions         according to the present invention comprise at least one         diaminotriazine compound of formula (I) and at least one further         active compound B (herbicide B).     -   According to a further embodiment of the invention the         compositions contain at least one inhibitor of the lipid         biosynthesis (herbicide b1). These are compounds that inhibit         lipid biosynthesis. Inhibition of the lipid biosynthesis can be         affected either through inhibition of acetylCoA carboxylase         (hereinafter termed ACC herbicides) or through a different mode         of action (hereinafter termed non-ACC herbicides). The ACC         herbicides belong to the group A of the HRAC classification         system whereas the non-ACC herbicides belong to the group N of         the HRAC classification.     -   According to a further embodiment of the invention the         compositions contain at least one ALS inhibitor (herbicide b2).         The herbicidal activity of these compounds is based on the         inhibition of acetolactate synthase and thus on the inhibition         of the branched chain amino acid biosynthesis. These inhibitors         belong to the group B of the HRAC classification system.     -   According to a further embodiment of the invention the         compositions contain at least one inhibitor of photosynthesis         (herbicide b3). The herbicidal activity of these compounds is         based either on the inhibition of the photosystem II in plants         (so-called PSII inhibitors, groups C1, C2 and C3 of HRAC         classification) or on diverting the electron transfer in         photosystem I in plants (so-called PSI inhibitors, group D of         HRAC classification) and thus on an inhibition of         photosynthesis. Amongst these, PSII inhibitors are preferred.     -   According to a further embodiment of the invention the         compositions contain at least one inhibitor of         protoporphyrinogen-IX-oxidase (herbicide b4). The herbicidal         activity of these compounds is based on the inhibition of the         protoporphyrinogen-IX-oxidase. These inhibitors belong to the         group E of the HRAC classification system.     -   According to a further embodiment of the invention the         compositions contain at least one bleacher-herbicide (herbicide         b5). The herbicidal activity of these compounds is based on the         inhibition of the carotenoid biosynthesis. These include         compounds which inhibit carotenoid biosynthesis by inhibition of         phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC         classification), compounds that inhibit the         4-hydroxyphenyl-pyruvate-dioxygenase (HPPD inhibitors, group F2         of HRAC classification), compounds that inhibit DOXsynthase         (group F4 of HRAC class) and compounds which inhibit carotenoid         biosynthesis by an unknown mode of action (bleacher—unknown         target, group F3 of HRAC classification).     -   According to a further embodiment of the invention the         compositions contain at least one EPSP synthase inhibitor         (herbicide b6). The herbicidal activity of these compounds is         based on the inhibition of enolpyruvyl shikimate 3-phosphate         synthase, and thus on the inhibition of the amino acid         biosynthesis in plants. These inhibitors belong to the group G         of the HRAC classification system.     -   According to a further embodiment of the invention the         compositions contain at least one glutamine synthetase inhibitor         (herbicide b7). The herbicidal activity of these compounds is         based on the inhibition of glutamine synthetase, and thus on the         inhibition of the aminoacid biosynthesis in plants. These         inhibitors belong to the group H of the HRAC classification         system.     -   According to an further embodiment of the invention the         compositions contain at least one DHP synthase inhibitor         (herbicide b8). The herbicidal activity of these compounds is         based on the inhibition of 7,8-dihydropteroate synthase. These         inhibitors belong to the group I of the HRAC classification         system.     -   According to a further embodiment of the invention the         compositions contain at least one mitosis inhibitor (herbicide         b9). The herbicidal activity of these compounds is based on the         disturbance or inhibition of microtubule formation or         organization, and thus on the inhibition of mitosis. These         inhibitors belong to the groups K1 and K2 of the HRAC         classification system. Among these, compounds of the group K1,         in particular dinitroanilines, are preferred.     -   According to a further embodiment of the invention the         compositions contain at least one VLCFA inhibitor (herbicide         b10). The herbicidal activity of these compounds is based on the         inhibition of the synthesis of very long chain fatty acids and         thus on the disturbance or inhibition of cell division in         plants. These inhibitors belong to the group K3 of the HRAC         classification system.     -   According to an further embodiment of the invention the         compositions contain at least one cellulose biosynthesis         inhibitor (herbicide b11). The herbicidal activity of these         compounds is based on the inhibition of the biosynthesis of         cellulose and thus on the inhibition of the synthesis of cell         walls in plants. These inhibitors belong to the group L of the         HRAC classification system.     -   According to a further embodiment of the invention the         compositions contain at least one decoupler herbicide (herbicide         b12). The herbicidal activity of these compounds is based on the         disruption of the cell membrane. These inhibitors belong to the         group M of the HRAC classification system.     -   According to a further embodiment of the invention the         compositions contain at least one auxinic herbicide (herbicide         b13). These include compounds that mimic auxins, i.e. plant         hormones, and affect the growth of the plants. These compounds         belong to the group O of the HRAC classification system.     -   According to a further embodiment of the invention the         compositions contain at least one auxin transport inhibitor         (herbicide b14). The herbicidal activity of these compounds is         based on the inhibition of the auxin transport in plants. These         compounds belong to the group P of the HRAC classification         system.     -   As to the given mechanisms of action and classification of the         active substances, see e.g. “HRAC, Classification of Herbicides         According to Mode of Action”,         http://www.plantprotection.org/hrac/MOA.html).

Preference is given to those compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1, b6, b9, b10 and b11.

-   -   Preference is also given to those compositions according to the         present invention comprising at least one herbicide B selected         from herbicides of class b2, b3, b4, b5, b6, b9 and b10.     -   Specific preference is given to those compositions according to         the present invention which comprise at least one herbicide B         selected from the herbicides of class b4, b6 b9 and b10.     -   Particular preference is given to those compositions according         to the present invention which comprise at least one herbicide B         selected from the herbicides of class b4, b6 and b10.     -   Examples of herbicides B which can be used in combination with         the diaminotriazine compounds of formula (I) according to the         present invention are:     -   b1) from the group of the lipid biosynthesis inhibitors:     -   ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim,         clethodim, clodinafop, clodinafop-propargyl, cycloxydim,         cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl,         fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl,         fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl,         haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl,         metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop,         quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P,         quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim,         tepraloxydim, tralkoxydim,     -   4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1312337-72-6);         4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1312337-45-3);         4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1033757-93-5);         4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione         (CAS 1312340-84-3);         5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1312337-48-6);         5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;         5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1312340-82-1);         5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1033760-55-2);         4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1312337-51-1);         4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester;         4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1312340-83-2);         4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1033760-58-5); and non ACC         herbicides such as benfuresate, butylate, cycloate, dalapon,         dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate,         molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb,         tiocarbazil, triallate and vernolate;     -   b2) from the group of the ALS inhibitors:     -   sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron,         bensulfuron-methyl, chlorimuron, chlorimuron-ethyl,         chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron,         ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,         flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium,         foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron,         iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron,         iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron,         metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron,         primisulfuron, primisulfuron-methyl, propyrisulfuron,         prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron,         sulfometuron, sulfometuron-methyl, sulfosulfuron,         thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron,         tribenuron-methyl, trifloxysulfuron, triflusulfuron,         triflusulfuron-methyl and tritosulfuron,     -   imidazolinones such as imazamethabenz, imazamethabenz-methyl,         imazamox, imazapic, imazapyr, imazaquin and imazethapyr,         triazolopyrimidine herbicides and sulfonanilides such as         cloransulam, cloransulam-methyl, diclosulam, flumetsulam,         florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam,     -   pyrimidinylbenzoates such as bispyribac, bispyribac-sodium,         pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl,         pyrithiobac, pyrithiobac-sodium,         4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic         acid-1-methylethyl ester (CAS 420138-41-6),         4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic         acid propyl ester (CAS 420138-40-5),         N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine         (CAS 420138-01-8),     -   sulfonylaminocarbonyl-triazolinone herbicides such as         flucarbazone, flucarbazone-sodium, propoxycarbazone,         propoxycarbazone-sodium, thiencarbazone and         thiencarbazone-methyl; and triafamone;     -   among these, a preferred embodiment of the invention relates to         those compositions comprising at least one imidazolinone         herbicide;     -   b3) from the group of the photosynthesis inhibitors:     -   amicarbazone, inhibitors of the photosystem II, e.g. triazine         herbicides, including of chlorotriazine, triazinones,         triazindiones, methylthiotriazines and pyridazinones such as         ametryn, atrazine, chloridazone, cyanazine, desmetryn,         dimethametryn, hexazinone, metribuzin, prometon, prometryn,         propazine, simazine, simetryn, terbumeton, terbuthylazin,         terbutryn and trietazin, aryl urea such as chlorobromuron,         chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron,         isoproturon, isouron, linuron, metamitron, methabenzthiazuron,         metobenzuron, metoxuron, monolinuron, neburon, siduron,         tebuthiuron and thiadiazuron, phenyl carbamates such as         desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl,         nitrile herbicides such as bromofenoxim, bromoxynil and its         salts and esters, ioxynil and its salts and esters, uraciles         such as bromacil, lenacil and terbacil, and bentazon and         bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil         and inhibitors of the photosystem I such as diquat,         diquat-dibromide, paraquat, paraquat-dichloride and         paraquat-dimetilsulfate. Among these, a preferred embodiment of         the invention relates to those compositions comprising at least         one aryl urea herbicide. Among these, likewise a preferred         embodiment of the invention relates to those compositions         comprising at least one triazine herbicide. Among these,         likewise a preferred embodiment of the invention relates to         those compositions comprising at least one nitrile herbicide;     -   b4) from the group of the protoporphyrinogen-IX oxidase         inhibitors:     -   acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,         benzfendizone, bifenox, butafenacil, carfentrazone,         carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate,         flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl,         flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet,         fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl,         oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil,         pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone,         thidiazimin, tiafenacil, trifludimoxazin (BAS 850 H), ethyl         [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate         (CAS 353292-31-6; S-3100; Sumitomo; LS 5296489),         N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide         (CAS 452098-92-9),         N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide         (CAS 915396-43-9),         N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide         (CAS 452099-05-7),         N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide         (CAS 452100-03-7),         3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione         (CAS 451484-50-7) (LS 4061013),         2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione         (CAS 1300118-96-0) (LS 567 0033=F2-Flumioxazin),         1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione         (CAS 1304113-05-0) (LS 568 1323=Uracil-F2-PPO), methyl         (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1         H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate         (CAS 948893-00-3) (Isagro, IR6396), and         3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione         (CAS 212754-02-4) (FMC Trifluoromethyluracil);     -   b5) from the group of the bleacher herbicides:     -   PDS inhibitors: beflubutamid, diflufenican, fluridone,         flurochloridone, flurtamone, norflurazon, picolinafen, and         4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine         (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap,         bicyclopyrone, clomazone, fenquintrione, isoxaflutole,         mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen,         sulcotrione, tefuryltrione, tembotrione, tolpyralate,         topramezone, bleacher, unknown target: aclonifen, amitrole and         flumeturon;     -   b6) from the group of the EPSP synthase inhibitors:     -   glyphosate, glyphosate-isopropylammonium, glyposate-potassium         and glyphosate-trimesium (sulfosate);     -   b7) from the group of the glutamine synthase inhibitors:     -   bilanaphos (bialaphos), bilanaphos-sodium, glufosinate,         glufosinate-P and glufosinate-ammonium;     -   b8) from the group of the DHP synthase inhibitors:     -   asulam;     -   b9) from the group of the mitosis inhibitors:     -   compounds of group K1: dinitroanilines such as benfluralin,         butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin,         pendimethalin, prodiamine and trifluralin, phosphoramidates such         as amiprophos, amiprophos-methyl, and butamiphos, benzoic acid         herbicides such as chlorthal, chlorthal-dimethyl, pyridines such         as dithiopyr and thiazopyr, benzamides such as propyzamide and         tebutam; compounds of group K2: carbetamide, chlorpropham,         flamprop, flamprop-isopropyl, flamprop-methyl,         flamprop-M-isopropyl, flamprop-M-methyl and propham; among         these, compounds of group K1, in particular dinitroanilines are         preferred;     -   b10) from the group of the VLCFA inhibitors:     -   chloroacetamides such as acetochlor, alachlor, butachlor,         dimethachlor, dimethenamid, dimethenamid-P, metazachlor,         metolachlor, metolachlor-S, pethoxamid, pretilachlor,         propachlor, propisochlor and thenylchlor, oxyacetanilides such         as flufenacet and mefenacet, acetanilides such as diphenamid,         naproanilide, napropamide and napropamide-M, tetrazolinones such         fentrazamide, and other herbicides such as anilofos,         cafenstrole, fenoxasulfone, ipfencarbazone, piperophos,         pyroxasulfone and isoxazoline compounds of the formulae II.1,         II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

the isoxazoline compounds of the formula (I)I are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576;

-   -   among the VLCFA inhibitors, preference is given to         chloroacetamides and oxyacetamides;     -   b11) from the group of the cellulose biosynthesis inhibitors:     -   chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben,         triaziflam and         1-cyclohexyl-5-pentafluorphenyloxy-1⁴-[1,2,4,6]thiatriazin-3-ylamine         (CAS 175899-01-1);     -   b12) from the group of the decoupler herbicides:     -   dinoseb, dinoterb and DNOC and its salts;     -   b13) from the group of the auxinic herbicides:     -   2,4-D and its salts and esters such as clacyfos, 2,4-DB and its         salts and esters, aminocyclopyrachlor and its salts and esters,         aminopyralid and its salts such as         aminopyralid-dimethylammonium,         aminopyralid-tris(2-hydroxypropyl)ammonium and its esters,         benazolin, benazolin-ethyl, chloramben and its salts and esters,         clomeprop, clopyralid and its salts and esters, dicamba and its         salts and esters, dichlorprop and its salts and esters,         dichlorprop-P and its salts and esters, fluroxypyr,         fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its         salts and esters (CAS 943832-60-8 DOW, LS 566509); MCPA and its         salts and esters, MCPA-thioethyl, MCPB and its salts and esters,         mecoprop and its salts and esters, mecoprop-P and its salts and         esters, picloram and its salts and esters, quinclorac,         quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and         its salts and esters,         4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic         acid (DOW, “Rinskor-acid”) and benzyl         4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate         (CAS 1390661-72-9) (DOW, “Rinskor”);     -   b14) from the group of the auxin transport inhibitors:         diflufenzopyr, diflufenzopyr-sodium, naptalam and         naptalam-sodium;     -   b15) from the group of the other herbicides: bromobutide,         chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron,         cyclopyrimorate (CAS 499223-49-3 Mitsui; SW-065; H-965) and its         salts and esters, dalapon, dazomet, difenzoquat,         difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and         its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol,         fosamine, fosamine-ammonium, indanofan, maleic hydrazide,         mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide,         methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid,         oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and         tridiphane.     -   Preferred herbicides B that can be used in combination with the         diaminotriazine compounds of the formula (I) according to the         present invention are:     -   b1) from the group of the lipid biosynthesis inhibitors:     -   clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl,         diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl,         haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim,         propaquizafop, quizalofop-P-ethyl, quizalofop-P-tefuryl,         sethoxydim, tepraloxydim, tralkoxydim,         4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1312337-72-6);         4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1312337-45-3);         4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1033757-93-5);         4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione         (CAS 1312340-84-3);         5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1312337-48-6);         5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;         5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1312340-82-1);         5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1033760-55-2);         4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1312337-51-1);         4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester;         4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1312340-83-2);         4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1033760-58-5); benfuresate,         dimepiperate, EPTC, esprocarb, ethofumesate, molinate,         orbencarb, prosulfocarb, thiobencarb and triallate;     -   b2) from the group of the ALS inhibitors:     -   amidosulfuron, azimsulfuron, bensulfuron-methyl,         bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron,         cloransulam-methyl, cyclosulfamuron, diclosulam,         ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,         florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam,         flupyrsulfuron-methyl-sodium, foramsulfuron,         halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic,         imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron,         iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium,         mesosulfuron, metazosulfuron, metosulam, metsulfuron-methyl,         nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam,         primisulfuron-methyl, propoxycarbazon-sodium, propyrisulfuron,         prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan,         pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, pyroxsulam,         rimsulfuron, sulfometuron-methyl, sulfosulfuron,         thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron,         tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl,         tritosulfuron and triafamone;     -   b3) from the group of the photosynthesis inhibitors:     -   ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium,         bromoxynil and its salts and esters, chloridazone,         chlorotoluron, cyanazine, desmedipham, diquat-dibromide, diuron,         fluometuron, hexazinone, ioxynil and its salts and esters,         isoproturon, lenacil, linuron, metamitron, methabenzthiazuron,         metribuzin, paraquat, paraquat-dichloride, phenmedipham,         propanil, pyridate, simazine, terbutryn, terbuthylazine and         thidiazuron;     -   b4) from the group of the protoporphyrinogen-IX oxidase         inhibitors:     -   acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil,         carfentrazone-ethyl, cinidon-ethyl, flufenpyr-ethyl,         flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl,         fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen,         pentoxazone, pyraflufen, pyraflufen-ethyl, saflufenacil,         sulfentrazone, tiafenacil, trifludimoxazin (BAS 850 H), ethyl         [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate         (CAS 353292-31-6; S-3100; Sumitomo; LS 5296489),         N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide         (CAS 452098-92-9),         N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide         (CAS 915396-43-9),         N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide         (CAS 452099-05-7),         N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide         (CAS 452100-03-7),         3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione         (CAS 451484-50-7) (LS 4061013),         2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione         (CAS 1300118-96-0) (LS 567 0033=F2-Flumioxazin);         1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione         (CAS 1304113-05-0) (LS 568 1323=Uracil-F2-PPO), and         3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione         (CAS 212754-02-4) (FMC Trifluoromethyluracil);     -   b5) from the group of the bleacher herbicides:     -   aclonifen, amitrole, beflubutamid, benzobicyclon, bicyclopyrone,         clomazone, diflufenican, fenquintrione, flumeturon,         flurochloridone, flurtamone, isoxaflutole, mesotrione,         norflurazon, picolinafen, pyrasulfotole, pyrazolynate,         sulcotrione, tefuryltrione, tembotrione, tolpyralate,         topramezone and         4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine         (CAS 180608-33-7);     -   b6) from the group of the EPSP synthase inhibitors:     -   glyphosate, glyphosate-isopropylammonium, glyphosate-potassium         and glyphosate-trimesium (sulfosate);     -   b7) from the group of the glutamine synthase inhibitors:     -   glufosinate, glufosinate-P, glufosinate-ammonium;     -   b8) from the group of the DHP synthase inhibitors: asulam;     -   b9) from the group of the mitosis inhibitors:     -   benfluralin, dithiopyr, ethalfluralin, flamprop,         flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl,         flamprop-M-methyl, oryzalin, pendimethalin, thiazopyr and         trifluralin;     -   b10) from the group of the VLCFA inhibitors:     -   acetochlor, alachlor, anilofos, butachlor, cafenstrole,         dimethenamid, dimethenamid-P, fentrazamide, flufenacet,         mefenacet, metazachlor, metolachlor, S-metolachlor,         naproanilide, napropamide, napropamide-M, pretilachlor,         fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and         isoxazoline-compounds of the formulae II.1, II.2, II.3, II.4,         II.5, II.6, II.7, II.8 and II.9 as mentioned above;     -   b11) from the group of the cellulose biosynthesis inhibitors:         dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and         1-cyclohexyl-5-pentafluorphenyloxy-1⁴-[1,2,4,6]thiatriazin-3-ylamine         (CAS 175899-01-1);     -   b13) from the group of the auxinic herbicides:     -   2,4-D and its salts and esters, aminocyclopyrachlor and its         salts and esters, aminopyralid and its salts such as         aminopyralid-dimethylammonium,         aminopyralid-tris(2-hydroxypropyl)ammonium and its esters,         clopyralid and its salts and esters, dicamba and its salts and         esters, dichlorprop-P and its salts and esters,         fluroxypyr-meptyl, halauxifen and its salts and esters (CAS         943832-60-8 DOW, LS 566509), MCPA and its salts and esters, MCPB         and its salts and esters, mecoprop-P and its salts and esters,         picloram and its salts and esters, quinclorac, quinmerac,         triclopyr and its salts and esters,         4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic         acid (DOW, “Rinskor-acid”) and benzyl         4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate         (CAS 1390661-72-9) (DOW, “Rinskor”);     -   b14) from the group of the auxin transport inhibitors:         diflufenzopyr and diflufenzopyr-sodium;     -   b15) from the group of the other herbicides: bromobutide,         cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3 Mitsui;         SW-065; H-965) and its salts and esters, dalapon, difenzoquat,         difenzoquat-metilsulfate, DSMA, dymron (=daimuron), indanofan,         metam, methylbromide, MSMA, oxaziclomefone, pyributicarb and         tridiphane.     -   Particularly preferred herbicides B that can be used in         combination with the diaminotriazine compounds of the         formula (I) according to the present invention are:     -   b1) from the group of the lipid biosynthesis inhibitors:         clodinafop-propargyl, cycloxydim, cyhalofop-butyl,         fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim,         tralkoxydim,         4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1312337-72-6);         4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1312337-45-3);         4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one         (CAS 1033757-93-5);         4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione         (CAS 1312340-84-3);         5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1312337-48-6);         5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;         5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1312340-82-1);         5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one         (CAS 1033760-55-2);         4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1312337-51-1);         4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester;         4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1312340-83-2);         4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl         carbonic acid methyl ester (CAS 1033760-58-5); esprocarb,         prosulfocarb, thiobencarb and triallate;     -   b2) from the group of the ALS inhibitors: bensulfuron-methyl,         bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam,         flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic,         imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron,         iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium,         mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam,         propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl,         pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl,         tritosulfuron and triafamone;     -   b3) from the group of the photosynthesis inhibitors: ametryn,         atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron,         metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn         and terbuthylazine;     -   b4) from the group of the protoporphyrinogen-IX oxidase         inhibitors: flumioxazin, oxyfluorfen, pyraflufen,         pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin         (BAS 850 H), ethyl         [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate         (CAS 353292-31-6; S-3100; Sumitomo; LS 5296489),         3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione         (CAS 451484-50-7) (LS 4061013),         2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione         (CAS 1300118-96-0) (LS 567 0033=F2-Flumioxazin), and         1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione         (CAS 1304113-05-0) (LS 568 1323=Uracil-F2-PPO);     -   b5) from the group of the bleacher herbicides: amitrole,         bicyclopyrone, clomazone, diflufenican, fenquintrione,         flumeturon, flurochloridone, isoxaflutole, mesotrione,         picolinafen, sulcotrione, tefuryltrione, tembotrione,         tolpyralate and topramezone;     -   b6) from the group of the EPSP synthase inhibitors: glyphosate,         glyphosate-isopropylammonium and glyphosate-trimesium         (sulfosate);     -   b7) from the group of the glutamine synthase inhibitors:         glufosinate, glufosinate-P and glufosinate-ammonium;     -   b9) from the group of the mitosis inhibitors: pendimethalin and         trifluralin;     -   b10) from the group of the VLCFA inhibitors: acetochlor,         cafenstrole, dimethenamid-P, fentrazamide, flufenacet,         mefenacet, metazachlor, metolachlor, S-metolachlor,         fenoxasulfone, ipfencarbazone and pyroxasulfone; likewise,         preference is given to isoxazoline compounds of the formulae         II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as         mentioned above;     -   b11) from the group of the cellulose biosynthesis inhibitors:         indaziflam, isoxaben and triaziflam;     -   b13) from the group of the auxinic herbicides: 2,4-D and its         salts and esters such as clacyfos, and aminocyclopyrachlor and         its salts and esters, aminopyralid and its salts and its esters,         clopyralid and its salts and esters, dicamba and its salts and         esters, fluroxypyr-meptyl, halauxifen, halauxifen-methyl,         quinclorac, quinmerac,         4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic         acid (DOW, “Rinskor-acid”) and benzyl         4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate         (CAS 1390661-72-9) (DOW, “Rinskor”);     -   b14) from the group of the auxin transport inhibitors:         diflufenzopyr and diflufenzopyr-sodium,     -   b15) from the group of the other herbicides: dymron (=daimuron),         indanofan, oxaziclomefone.

Particularly preferred herbicides B are the herbicides B as defined above; in particular the herbicides B.1-B.196 listed below in table B:

TABLE B Herbicide B B.1 clethodim B.2 clodinafop-propargyl B.3 cycloxydim B.4 cyhalofop-butyl B.5 fenoxaprop-ethyl B.6 fenoxaprop-P-ethyl B.7 metamifop B.8 pinoxaden B.9 profoxydim B.10 sethoxydim B.11 tepraloxydim B.12 tralkoxydim B.13 esprocarb B.14 ethofumesate B.15 molinate B.16 prosulfocarb B.17 thiobencarb B.18 triallate B.19 bensulfuron-methyl B.20 bispyribac-sodium B.21 cloransulam-methyl B.22 chlorsulfuron B.23 clorimuron B.24 cyclosulfamuron B.25 diclosulam B.26 florasulam B.27 flumetsulam B.28 flupyrsulfuron-methyl-sodium B.29 foramsulfuron B.30 imazamox B.31 imazamox-ammonium B.32 imazapic B.33 imazapic-ammonium B.34 imazapic-isopropylammonium B.35 imazapyr B.36 imazapyr-ammonium B.37 imazapyr-isopropylammonium B.38 imazaquin B.39 imazaquin-ammonium B.40 imazethapyr B.41 imazethapyr-ammonium B.42 imazethapyr-isopropylammonium B.43 imazosulfuron B.44 iodosulfuron-methyl-sodium B.45 iofensulfuron B.46 iofensulfuron-sodium B.47 mesosulfuron-methyl B.48 metazosulfuron B.49 metsulfuron-methyl B.50 metosulam B.51 nicosulfuron B.52 penoxsulam B.53 propoxycarbazon-sodium B.54 pyrazosulfuron-ethyl B.55 pyribenzoxim B.56 pyriftalid B.57 pyroxsulam B.58 propyrisulfuron B.59 rimsulfuron B.60 sulfosulfuron B.61 thiencarbazone-methyl B.62 thifensulfuron-methyl B.63 tribenuron-methyl B.64 tritosulfuron B.65 triafamone B.66 ametryne B.67 atrazine B.68 bentazon B.69 bromoxynil B.70 bromoxynil-octanoate B.71 bromoxynil-heptanoate B.72 bromoxynil-potassium B.73 diuron B.74 fluometuron B.75 hexazinone B.76 isoproturon B.77 linuron B.78 metamitron B.79 metribuzin B.80 propanil B.81 simazin B.82 terbuthylazine B.83 terbutryn B.84 paraquat-dichloride B.85 acifluorfen B.86 butafenacil B.87 carfentrazone-ethyl B.88 flumioxazin B.89 fomesafen B.90 oxadiargyl B.91 oxyfluorfen B.92 pyraflufen B.93 pyraflufen-ethyl B.94 saflufenacil B.95 sulfentrazone B.96 trifludimoxazin (BAS 850 H) B.97 ethyl [3-[2-chloro-4-fluoro- 5-(1-methyl-6-trifluoromethyl- 2,4-dioxo-1,2,3,4-tetrahydro- pyrimidin-3-yl)phenoxy]-2- pyridyloxy]acetate (CAS 353292-31-6) Sumitomo; LS 5296489 B.98 benzobicyclon B.99 bicyclopyrone B.100 clomazone B.101 diflufenican B.102 flurochloridone B.103 isoxaflutole B.104 mesotrione B.105 norflurazone B.106 picolinafen B.107 sulcotrione B.108 tefuryltrione B.109 tembotrione B.110 tolpyralate B.111 topramezone B.112 topramezone-sodium B.113 amitrole B.114 fluometuron B.115 fenquintrione B.116 glyphosate B.117 glyphosate-ammonium B.118 glyphosate-dimethylammonium B.119 glyphosate-isopropylammonium B.120 glyphosate-trimesium (sulfosate) B.121 glyphosate-potassium B.122 glufosinate B.123 glufosinate-ammonium B.124 glufosinate-P B.125 glufosinate-P-ammonium B.126 pendimethalin B.127 trifluralin B.128 acetochlor B.129 butachlor B.130 cafenstrole B.131 dimethenamid-P B.132 fentrazamide B.133 flufenacet B.134 mefenacet B.135 metazachlor B.136 metolachlor B.137 S-metolachlor B.138 pretilachlor B.139 fenoxasulfone B.140 indaziflam B.141 isoxaben B.142 triaziflam B.143 ipfencarbazone B.144 pyroxasulfone B.145 2,4-D B.146 2,4-D-isobutyl B.147 2,4-D-dimethylammonium B.148 2,4-D-N,N,N-trimethylethanolammonium B.149 aminopyralid B.150 aminopyralid-methyl B.151 aminopyralid-dimethyl-ammonium B.152 aminopyralid-tris(2-hydroxypropyl)ammonium B.153 clopyralid B.154 clopyralid-methyl B.155 clopyralid-olamine B.156 dicamba B.157 dicamba-butotyl B.158 dicamba-diglycolamine B.159 dicamba-dimethylammonium B.160 dicamba-diolamine B.161 dicamba-isopropylammonium B.162 dicamba-potassium B.163 dicamba-sodium B.164 dicamba-trolamine B.165 dicamba-N,N-bis-(3-aminopropyl)methylamine B.166 dicamba-diethylenetriamine B.167 fluroxypyr B.168 fluroxypyr-meptyl B.169 halauxifen B.170 halauxifen-methyl B.171 MCPA B.172 MCPA-2-ethylhexyl B.173 MCPA-dimethylammonium B.174 quinclorac B.175 quinclorac-dimethylammonium B.176 quinmerac B.177 quinmerac-dimethylammonium B.178 4-amino-3-chloro-6-(4-chloro-2- fluoro-3-methoxyphenyl)-5- fluoropyridine-2-carboxylic acid (DOW, “Rinskor-acid”) B.179 benzyl 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxy- phenyl)-5-fluoropyridine-2- carboxylate (CAS 1390661-72-9) (DOW, “Rinskor”) B.180 aminocyclopyrachlor B.181 aminocyclopyrachlor-potassium B.182 aminocyclopyrachlor-methyl B.183 diflufenzopyr B.184 diflufenzopyr-sodium B.185 dymron B.186 indanofan B.187 oxaziclomefone B.188 II.1 B.189 II.2 B.190 II.3 B.191 II.4 B.192 II.5 B.193 II.6 B.194 II.7 B.195 II.8 B.196 II.9

In another embodiment of the present invention the compositions according to the present invention comprise at least one diaminotriazine compound of formula (I) and at least one safener C.

Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the present compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant. The safeners and the diaminotriazine compound of formula (I) and/or the herbicides B can be applied simultaneously or in succession.

Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.

Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4) and N-(2-Methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-12-0).

Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro-[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4) and N-(2-Methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-12-0).

Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic anhydride, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4) and N-(2-Methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-12-0).

Particularly preferred safeners C, which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1-C.17 listed below in table C:

TABLE C Safener C C.1 benoxacor C.2 cloquintocet C.3 cloquintocet-mexyl C.4 cyprosulfamide C.5 dichlormid C.6 fenchlorazole C.7 fenchlorazole-ethyl C.8 fenclorim C.9 furilazole C.10 isoxadifen C.11 isoxadifen-ethyl C.12 mefenpyr C.13 mefenpyr-diethyl C.14 naphtalic acid anhydride C.15 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) C.16 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4) C.17 N-(2-Methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-12-0)

The active compounds B of groups b1) to b15) and the active compounds C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS No. 52836-31-4] is also referred to as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.

The assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this substance was only assigned to one mechanism of action.

Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative in the compositions according to the invention.

In the case of dicamba, suitable salts include those, where the counterion is an agriculturally acceptable cation. For example, suitable salts of dicamba are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of a suitable ester are dicamba-methyl and dicamba-butotyl.

Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanol-ammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)-ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium. Examples of suitable esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.

Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethylammonium. Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl.

Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isoctyl.

Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.

A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.

Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2-hydroxypropyl)ammonium. Example of suitable esters of clopyralid is clopyralid-methyl.

Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1-methylethyl, wherein fluroxypyr-meptyl is preferred.

Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.

A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are for example triclopyr-ethyl and triclopyr-butotyl.

Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium and 2,3,6-TBA-sodium.

Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid-dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.

Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).

A suitable salt of glufosinate is for example glufosinate-ammonium.

A suitable salt of glufosinate-P is for example glufosinate-P-ammonium.

Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.

Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.

Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.

A suitable salt of naptalam is for example naptalam-sodium.

Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor-dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.

A suitable salt of quinclorac is for example quinclorac-dimethylammonium.

A suitable salt of quinmerac is for example quinmerac-dimethylammonium.

A suitable salt of imazamox is for example imazamox-ammonium.

Suitable salts of imazapic are for example imazapic-ammonium and imazapic-isopropylammonium.

Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr-isopropylammonium.

A suitable salt of imazaquin is for example imazaquin-ammonium.

Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr-isopropylammonium.

A suitable salt of topramezone is for example topramezone-sodium.

According to a preferred embodiment of the invention, the composition comprises as herbicidal active compound B or component B at least one, preferably exactly one herbicide B.

According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least two, preferably exactly two herbicides B different from each other.

According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least three, preferably exactly three herbicides B different from each other.

According to another preferred embodiment of the invention, the composition comprises as safening component C or component C at least one, preferably exactly one safener C.

According to another preferred embodiment of the invention, the composition comprises as component B at least one, preferably exactly one herbicide B, and as component C at least one, preferably exactly one, safener C.

According to another preferred embodiment of the invention, the composition comprises at least two, preferably exactly two, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.

According to another preferred embodiment of the invention, the composition comprises at least three, preferably exactly three, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.

According to another preferred embodiment of the invention, the composition comprises at least one, preferably exactly one compound of formula (I) and as component B at least one, preferably exactly one, herbicide B.

According to another preferred embodiment of the invention, the composition comprises at least one, preferably exactly one compound of formula (I) and at least two, preferably exactly two, herbicides B different from each other.

According to another preferred embodiment of the invention, the composition comprises at least one, preferably exactly one compound of formula (I) and at least three, preferably exactly three, herbicides B different from each other.

According to another preferred embodiment of the invention, the composition comprises at least one, preferably exactly one compound of formula (I) and as component C at least one, preferably exactly one, safener C.

According to another preferred embodiment of the invention, the composition comprises at least one, preferably exactly one compound of formula (I) as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.

According to another preferred embodiment of the invention, the composition comprises at least one, preferably exactly one compound of formula (I), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.

According to another preferred embodiment of the invention, the composition comprises at least one, preferably exactly one compound of formula (I) at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b1), in particular selected from the group consisting of clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, esprocarb, prosulfocarb, thiobencarb and triallate.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b2), in particular selected from the group consisting of bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazon-sodium, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl and tritosulfuron.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn and terbuthylazine.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b4), in particular selected from the group consisting of flumioxazin, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin (BAS 850 H), ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100; Sumitomo; LS 5296489), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7) LS 4061013), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS 1300118-96-0) (LS 5670033=F2-Flumioxazin) and 1-methyl-6-trifluoro-methyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0) (LS 568 1323=Uracil-F2-PPO).

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b5), in particular selected from the group consisting of amitrole, bicyclopyrone, clomazone, diflufenican, flumeturon, flurochloridone, isoxaflutole, mesotrione, picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate and topramezone.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b6), in particular selected from the group consisting of glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b7), in particular selected from the group consisting of glufosinate, glufosinate-P and glufosinate-ammonium.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b9), in particular selected from the group consisting of pendimethalin and trifluralin.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of acetochlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone and pyroxasulfone. Likewise, preference is given to compositions comprising in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of isoxazoline compounds of the formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b11), in particular indaziflam, isoxaben and triaziflam.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b13), in particular selected from the group consisting of 2,4-D and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, fluroxypyr-meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid (DOW, “Rinskor-acid”) and benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9) (DOW, “Rinskor”).

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b14), in particular selected from the group consisting of diflufenzopyr and diflufenzopyr-sodium.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one herbicidally active compound from group b15), in particular selected from the group consisting of dymron (=daimuron), indanofan and oxaziclomefone.

According to another preferred embodiment of the invention, the composition comprises, in addition to a compounds of formula (I), at least one and especially exactly one safener C, in particular selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4).

Further preferred embodiments relate to ternary compositions which correspond to the binary compositions mentioned above and additionally comprise a safener C, in particular selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4).

Here and below, the term “binary compositions” includes compositions comprising one or more, for example 1, 2 or 3, active compounds of the formula (I) and either one or more, for example 1, 2 or 3, herbicides B or one or more safeners C.

Correspondingly, the term “ternary compositions” includes compositions comprising one or more, for example 1, 2 or 3, active compounds of the formula (I), one or more, for example 1, 2 or 3, herbicides B and one or more, for example 1, 2 or 3, safeners C.

In binary compositions comprising at least one compound of the formula (I) as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula (I) as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

In ternary compositions comprising at least one compound of formula (I) as component A, at least one herbicide B and at least one safener C, the relative proportions by weight of the components A:B are generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1, the weight ratio of the components A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1, and the weight ratio of the components B:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1. The weight ratio of components A+B to component C is preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

The weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.

Particularly preferred are the compositions mentioned below comprising the compounds of formula (I) as defined and the substance(s) as defined in the respective row of table 1;

especially preferred comprising as only herbicidal active compounds the compounds of formula (I) as defined and the substance(s) as defined in the respective row of table 1;

most preferably comprising as only active compounds the compounds of formula I as defined and the substance(s) as defined in the respective row of table 1.

Particularly preferred are compositions 1.1 to 1.3545, comprising the compounds of formula (I) and the substance(s) as defined in the respective row of table 1:

The following combinations indicated by the code A-X.Y.Z represent particular embodiments of the invention:

A-1.1.1 to A-1.727.3545,

A-2.1.1 to A-2.727.3545,

A-3.1.1 to A-3.727.3545,

A-4.1.1 to A-4.727.3545,

A-5.1.1 to A-5.727.3545,

A-6.1.1 to A-6.727.3545,

A-7.1.1 to A-7.727.3545,

A-8.1.1 to A-8.727.3545,

A-9.1.1 to A-9.727.3545,

A-10.1.1 to A-10.727.3545,

A-11.1.1 to A-11.727.3545,

A-12.1.1 to A-12.727.3545,

A-13.1.1 to A-13.727.3545,

A-14.1.1 to A-14.727.3545,

A-15.1.1 to A-15.727.3545,

A-16.1.1 to A-16.727.3545,

A-17.1.1 to A-17.727.3545,

A-18.1.1 to A-18.727.3545,

A-19.1.1 to A-19.727.3545,

A-20.1.1 to A-20.727.3545,

A-21.1.1 to A-21.727.3545,

A-22.1.1 to A-22.727.3545,

A-23.1.1 to A-23.727.3545,

A-24.1.1 to A-24.727.3545,

A-25.1.1 to A-25.727.3545,

A-26.1.1 to A-26.727.3545,

A-27.1.1 to A-27.727.3545,

A-28.1.1 to A-28.727.3545,

A-29.1.1 to A-29.727.3545,

A-30.1.1 to A-30.727.3545,

A-31.1.1 to A-31.727.3545,

A-32.1.1 to A-32.727.3545,

A-33.1.1 to A-33.727.3545,

A-34.1.1 to A-34.727.3545,

A-35.1.1 to A-35.727.3545,

A-36.1.1 to A-36.727.3545.

In the above codes A-X refers to the numbers of tables A-1 to A.36. The integer Y refers to the row of table A, while the integer Z refers to the row of table 1 below.

Hence, the code A-1.1.1 refers to the combination of the compound of formula I.a of table A-1, wherein X and R² are as defined in row 1 of table A, with the combination of the herbicide B and the safener C are as defined in combination no. 1.1 of table 1.

The code A-12.2.36 refers to the combination of the compound of formula I.a of table A-12, wherein X and R² are as defined in row 2 of table A, with the combination of the herbicide B and the safener C are as defined in combination no. 1.35 of table 1.

The code A-36.300. 3545 refers to the combination of the compound of formula I.a of table A-36, wherein X and R² are as defined in row 300 of table A, with the combination of the herbicide B and the safener C are as defined in combination no. 1.3545 of table 1.

Likewise the following combinations indicated by the code B-X.Y.Z represent particular embodiments of the invention:

B-1.1.1 to B-1.52.3545,

B-2.1.1 to B-2.52.3545,

B-3.1.1 to B-3.52.3545,

B-4.1.1 to B-4.52.3545,

B-5.1.1 to B-5.52.3545,

B-6.1.1 to B-6.52.3545,

B-7.1.1 to B-7.52.3545,

B-8.1.1 to B-8.52.3545,

B-9.1.1 to B-9.52.3545,

B-10.1.1 to B-10.52.3545,

B-11.1.1 to B-11.52.3545,

B-12.1.1 to B-12.52.3545,

B-13.1.1 to B-13.52.3545,

B-14.1.1 to B-14.52.3545,

B-15.1.1 to B-15.52.3545,

B-16.1.1 to B-16.52.3545,

B-17.1.1 to B-17.52.3545,

B-18.1.1 to B-18.52.3545,

B-19.1.1 to B-19.52.3545,

B-20.1.1 to B-20.52.3545,

B-21.1.1 to B-21.52.3545,

B-22.1.1 to B-22.52.3545,

B-23.1.1 to B-23.52.3545,

B-24.1.1 to B-24.52.3545,

B-25.1.1 to B-25.52.3545,

B-26.1.1 to B-26.52.3545,

B-27.1.1 to B-27.52.3545,

B-28.1.1 to B-28.52.3545,

B-29.1.1 to B-29.52.3545,

B-30.1.1 to B-30.52.3545,

B-31.1.1 to B-31.52.3545,

B-32.1.1 to B-32.52.3545,

B-33.1.1 to B-33.52.3545,

B-34.1.1 to B-34.52.3545,

B-35.1.1 to B-35.52.3545.

B-36.1.1 to B-36.52.3545.

In the above codes B-X refers to the numbers of tables B-1 to B.36. The integer Y refers to the row of table B, while the integer Z refers to the row of table 1 below.

Hence, the code B-1.1.1 refers to the combination of the compound of formula I.b of table B-1, wherein X and R² are as defined in row 1 of table B, with the combination of the herbicide B and the safener C are as defined in combination no. 1.1 of table 1.

The code B-12.2.36 refers to the combination of the compound of formula I.b of table B-12, wherein X and R² are as defined in row 2 of table B, with the combination of the herbicide B and the safener C are as defined in combination no. 1.36 of table 1.

The code B-36.50. 3545 refers to the combination of the compound of formula I.b of table B-36, wherein X and R² are as defined in row 50 of table B, with the combination of the herbicide B and the safener C are as defined in combination no. 1.3545 of table 1.

Likewise the following combinations indicated by the code C-X.Y.Z represent particular embodiments of the invention:

C-1.1.1 to C-1.8.3545,

C-2.1.1 to C-2.8.3545,

C-3.1.1 to C-3.8.3545,

C-4.1.1 to C-4.8.3545,

C-5.1.1 to C-5.8.3545,

C-6.1.1 to C-6.8.3545,

C-7.1.1 to C-7.8.3545,

C-8.1.1 to C-8.8.3545,

C-9.1.1 to C-9.8.3545,

C-10.1.1 to C-10.8.3545,

C-11.1.1 to C-11.8.3545,

C-12.1.1 to C-12.8.3545,

C-13.1.1 to C-13.8.3545,

C-14.1.1 to C-14.8.3545,

C-15.1.1 to C-15.8.3545,

C-16.1.1 to C-16.8.3545,

C-17.1.1 to C-17.8.3545,

C-18.1.1 to C-18.8.3545,

C-19.1.1 to C-19.8.3545,

C-20.1.1 to C-20.8.3545,

C-21.1.1 to C-21.8.3545,

C-22.1.1 to C-22.8.3545,

C-23.1.1 to C-23.8.3545,

C-24.1.1 to C-24.8.3545,

C-25.1.1 to C-25.8.3545,

C-26.1.1 to C-26.8.3545,

C-27.1.1 to C-27.8.3545,

C-28.1.1 to C-28.8.3545,

C-29.1.1 to C-29.8.3545,

C-30.1.1 to C-30.8.3545,

C-31.1.1 to C-31.8.3545,

C-32.1.1 to C-32.8.3545,

C-33.1.1 to C-33.8.3545,

C-34.1.1 to C-34.8.3545,

C-35.1.1 to C-35.8.3545.

C-36.1.1 to C-36.8.3545.

In the above codes C-X refers to the numbers of tables C-1 to C.36. The integer Y refers to the row of table C, while the integer Z refers to the row of table 1 below.

Hence, the code C-1.1.1 refers to the combination of the compound of formula I.c of table C-1, wherein X and R² are as defined in row 1 of table C, with the combination of the herbicide C and the safener C are as defined in combination no. 1.1 of table 1.

The code C-12.2.36 refers to the combination of the compound of formula I.c of table C-12, wherein X and R² are as defined in row 2 of table C, with the combination of the herbicide C and the safener C are as defined in combination no. 1.36 of table 1.

The code C-36.8. 3545 refers to the combination of the compound of formula I.c of table C-36, wherein X and R² are as defined in row 8 of table C, with the combination of the herbicide C and the safener C are as defined in combination no. 1.3545 of table 1.

TABLE 1 (compositions 1.1 to 1.3545): comp. no. herbcide B safener C 1.1 B.1 — 1.2 B.2 — 1.3 B.3 — 1.4 B.4 — 1.5 B.5 — 1.6 B.6 — 1.7 B.7 — 1.8 B.8 — 1.9 B.9 — 1.10 B.10 — 1.11 B.11 — 1.12 B.12 — 1.13 B.13 — 1.14 B.14 — 1.15 B.15 — 1.16 B.16 — 1.17 B.17 — 1.18 B.18 — 1.19 B.19 — 1.20 B.20 — 1.21 B.21 — 1.22 B.22 — 1.23 B.23 — 1.24 B.24 — 1.25 B.25 — 1.26 B.26 — 1.27 B.27 — 1.28 B.28 — 1.29 B.29 — 1.30 B.30 — 1.31 B.31 — 1.32 B.32 — 1.33 B.33 — 1.34 B.34 — 1.35 B.35 — 1.36 B.36 — 1.37 B.37 — 1.38 B.38 — 1.39 B.39 — 1.40 B.40 — 1.41 B.41 — 1.42 B.42 — 1.43 B.43 — 1.44 B.44 — 1.45 B.45 — 1.46 B.46 — 1.47 B.47 — 1.48 B.48 — 1.49 B.49 — 1.50 B.50 — 1.51 B.51 — 1.52 B.52 — 1.53 B.53 — 1.54 B.54 — 1.55 B.55 — 1.56 B.56 — 1.57 B.57 — 1.58 B.58. — 1.59 B.59 — 1.60 B.60 — 1.61 B.61 — 1.62 B.62 — 1.63 B.63 — 1.64 B.64 — 1.65 B.65 — 1.66 B.66 — 1.67 B.67 — 1.68 B.68 — 1.69 B.69 — 1.70 B.70 — 1.71 B.71 — 1.72 B.72 — 1.73 B.73 — 1.74 B.74 — 1.75 B.75 — 1.76 B.76 — 1.77 B.77 — 1.78 B.78 — 1.79 B.79 — 1.80 B.80 — 1.81 B.81 — 1.82 B.82 — 1.83 B.83 — 1.84 B.84 — 1.85 B.85 — 1.86 B.86 — 1.87 B.87 — 1.88 B.88 — 1.89 B.89 — 1.90 B.90 — 1.91 B.91 — 1.92 B.92 — 1.93 B.93 — 1.94 B.94 — 1.95 B.95 — 1.96 B.96 — 1.97 B.97 — 1.98 B.98 — 1.99 B.99 — 1.100 B.100 — 1.101 B.101 — 1.102 B.102 — 1.103 B.103 — 1.104 B.104 — 1.105 B.105 — 1.106 B.106 — 1.107 B.107 — 1.108 B.108 — 1.109 B.109 — 1.110 B.110 — 1.111 B.111 — 1.112 B.112 — 1.113 B.113 — 1.114 B.114 — 1.115 B.115 — 1.116 B.116 — 1.117 B.117 — 1.118 B.118 — 1.119 B.119 — 1.120 B.120 — 1.121 B.121 — 1.122 B.122 — 1.123 B.123 — 1.124 B.124 — 1.125 B.125 — 1.126 B.126 — 1.127 B.127 — 1.128 B.128 — 1.129 B.129 — 1.130 B.130 — 1.131 B.131 — 1.132 B.132 — 1.133 B.133 — 1.134 B.134 — 1.135 B.135 — 1.136 B.136 — 1.137 B.137 — 1.138 B.138 — 1.139 B.139 — 1.140 B.140 — 1.141 B.141 — 1.142 B.142 — 1.143 B.143 — 1.144 B.144 — 1.145 B.145 — 1.146 B.146 — 1.147 B.147 — 1.148 B.148 — 1.149 B.149 — 1.150 B.150 — 1.151 B.151 — 1.152 B.152 — 1.153 B.153 — 1.154 B.154 — 1.155 B.155 — 1.156 B.156 — 1.157 B.157 — 1.158 B.158 — 1.159 B.159 — 1.160 B.160 — 1.161 B.161 — 1.162 B.162 — 1.163 B.163 — 1.164 B.164 — 1.165 B.165 — 1.166 B.166 — 1.167 B.167 — 1.168 B.168 — 1.169 B.169 — 1.170 B.170 — 1.171 B.171 — 1.172 B.172 — 1.173 B.173 — 1.174 B.174 — 1.175 B.175 — 1.176 B.176 — 1.177 B.177 — 1.178 B.178 — 1.179 B.179 — 1.180 B.180 — 1.181 B.181 — 1.182 B.182 — 1.183 B.183 — 1.184 B.184 — 1.185 B.185 — 1.186 B.186 — 1.187 B.187 — 1.188 B.188 — 1.189 B.189 — 1.190 B.190 1.191 B.191 1.192 B.192 1.193 B.193 1.194 B.194 1.195 B.195 1.196 B.196 1.197 B.1 C.1 1.198 B.2 C.1 1.199 B.3 C.1 1.200 B.4 C.1 1.201 B.5 C.1 1.202 B.6 C.1 1.203 B.7 C.1 1.204 B.8 C.1 1.205 B.9 C.1 1.206 B.10 C.1 1.207 B.11 C.1 1.208 B.12 C.1 1.209 B.13 C.1 1.210 B.14 C.1 1.211 B.15 C.1 1.212 B.16 C.1 1.213 B.17 C.1 1.214 B.18 C.1 1.215 B.19 C.1 1.216 B.20 C.1 1.217 B.21 C.1 1.218 B.22 C.1 1.219 B.23 C.1 1.220 B.24 C.1 1.221 B.25 C.1 1.222 B.26 C.1 1.223 B.27 C.1 1.224 B.28 C.1 1.225 B.29 C.1 1.226 B.30 C.1 1.227 B.31 C.1 1.228 B.32 C.1 1.229 B.33 C.1 1.230 B.34 C.1 1.231 B.35 C.1 1.232 B.36 C.1 1.233 B.37 C.1 1.234 B.38 C.1 1.235 B.39 C.1 1.236 B.40 C.1 1.237 B.41 C.1 1.238 B.42 C.1 1.239 B.43 C.1 1.240 B.44 C.1 1.241 B.45 C.1 1.242 B.46 C.1 1.243 B.47 C.1 1.244 B.48 C.1 1.245 B.49 C.1 1.246 B.50 C.1 1.247 B.51 C.1 1.248 B.52 C.1 1.249 B.53 C.1 1.250 B.54 C.1 1.251 B.55 C.1 1.252 B.56 C.1 1.253 B.57 C.1 1.254 B.58. C.1 1.255 B.59 C.1 1.256 B.60 C.1 1.257 B.61 C.1 1.258 B.62 C.1 1.259 B.63 C.1 1.260 B.64 C.1 1.261 B.65 C.1 1.262 B.66 C.1 1.263 B.67 C.1 1.264 B.68 C.1 1.265 B.69 C.1 1.266 B.70 C.1 1.267 B.71 C.1 1.268 B.72 C.1 1.269 B.73 C.1 1.270 B.74 C.1 1.271 B.75 C.1 1.272 B.76 C.1 1.273 B.77 C.1 1.274 B.78 C.1 1.275 B.79 C.1 1.276 B.80 C.1 1.277 B.81 C.1 1.278 B.82 C.1 1.279 B.83 C.1 1.280 B.84 C.1 1.281 B.85 C.1 1.282 B.86 C.1 1.283 B.87 C.1 1.284 B.88 C.1 1.285 B.89 C.1 1.286 B.90 C.1 1.287 B.91 C.1 1.288 B.92 C.1 1.289 B.93 C.1 1.290 B.94 C.1 1.291 B.95 C.1 1.292 B.96 C.1 1.293 B.97 C.1 1.294 B.98 C.1 1.295 B.99 C.1 1.296 B.100 C.1 1.297 B.101 C.1 1.298 B.102 C.1 1.299 B.103 C.1 1.300 B.104 C.1 1.301 B.105 C.1 1.302 B.106 C.1 1.303 B.107 C.1 1.304 B.108 C.1 1.305 B.109 C.1 1.306 B.110 C.1 1.307 B.111 C.1 1.308 B.112 C.1 1.309 B.113 C.1 1.310 B.114 C.1 1.311 B.115 C.1 1.312 B.116 C.1 1.313 B.117 C.1 1.314 B.118 C.1 1.315 B.119 C.1 1.316 B.120 C.1 1.317 B.121 C.1 1.318 B.122 C.1 1.319 B.123 C.1 1.320 B.124 C.1 1.321 B.125 C.1 1.322 B.126 C.1 1.323 B.127 C.1 1.324 B.128 C.1 1.325 B.129 C.1 1.326 B.130 C.1 1.327 B.131 C.1 1.328 B.132 C.1 1.329 B.133 C.1 1.330 B.134 C.1 1.331 B.135 C.1 1.332 B.136 C.1 1.333 B.137 C.1 1.334 B.138 C.1 1.335 B.139 C.1 1.336 B.140 C.1 1.337 B.141 C.1 1.338 B.142 C.1 1.339 B.143 C.1 1.340 B.144 C.1 1.341 B.145 C.1 1.342 B.146 C.1 1.343 B.147 C.1 1.344 B.148 C.1 1.345 B.149 C.1 1.346 B.150 C.1 1.347 B.151 C.1 1.348 B.152 C.1 1.349 B.153 C.1 1.350 B.154 C.1 1.351 B.155 C.1 1.352 B.156 C.1 1.353 B.157 C.1 1.354 B.158 C.1 1.355 B.159 C.1 1.356 B.160 C.1 1.357 B.161 C.1 1.358 B.162 C.1 1.359 B.163 C.1 1.360 B.164 C.1 1.361 B.165 C.1 1.362 B.166 C.1 1.363 B.167 C.1 1.364 B.168 C.1 1.365 B.169 C.1 1.366 B.170 C.1 1.367 B.171 C.1 1.368 B.172 C.1 1.369 B.173 C.1 1.370 B.174 C.1 1.371 B.175 C.1 1.372 B.176 C.1 1.373 B.177 C.1 1.374 B.178 C.1 1.375 B.179 C.1 1.376 B.180 C.1 1.377 B.181 C.1 1.378 B.182 C.1 1.379 B.183 C.1 1.380 B.184 C.1 1.381 B.185 C.1 1.382 B.186 C.1 1.383 B.187 C.1 1.384 B.188 C.1 1.385 B.189 C.1 1.386 B.190 C.1 1.387 B.191 C.1 1.388 B.192 C.1 1.389 B.193 C.1 1.390 B.194 C.1 1.391 B.195 C.1 1.392 B.196 C.1 1.393 B.1 C.2 1.394 B.2 C.2 1.395 B.3 C.2 1.396 B.4 C.2 1.397 B.5 C.2 1.398 B.6 C.2 1.399 B.7 C.2 1.400 B.8 C.2 1.401 B.9 C.2 1.402 B.10 C.2 1.403 B.11 C.2 1.404 B.12 C.2 1.405 B.13 C.2 1.406 B.14 C.2 1.407 B.15 C.2 1.408 B.16 C.2 1.409 B.17 C.2 1.410 B.18 C.2 1.411 B.19 C.2 1.412 B.20 C.2 1.413 B.21 C.2 1.414 B.22 C.2 1.415 B.23 C.2 1.416 B.24 C.2 1.417 B.25 C.2 1.418 B.26 C.2 1.419 B.27 C.2 1.420 B.28 C.2 1.421 B.29 C.2 1.422 B.30 C.2 1.423 B.31 C.2 1.424 B.32 C.2 1.425 B.33 C.2 1.426 B.34 C.2 1.427 B.35 C.2 1.428 B.36 C.2 1.429 B.37 C.2 1.430 B.38 C.2 1.431 B.39 C.2 1.432 B.40 C.2 1.433 B.41 C.2 1.434 B.42 C.2 1.435 B.43 C.2 1.436 B.44 C.2 1.437 B.45 C.2 1.438 B.46 C.2 1.439 B.47 C.2 1.440 B.48 C.2 1.441 B.49 C.2 1.442 B.50 C.2 1.443 B.51 C.2 1.444 B.52 C.2 1.445 B.53 C.2 1.446 B.54 C.2 1.447 B.55 C.2 1.448 B.56 C.2 1.449 B.57 C.2 1.450 B.58. C.2 1.451 B.59 C.2 1.452 B.60 C.2 1.453 B.61 C.2 1.454 B.62 C.2 1.455 B.63 C.2 1.456 B.64 C.2 1.457 B.65 C.2 1.458 B.66 C.2 1.459 B.67 C.2 1.460 B.68 C.2 1.461 B.69 C.2 1.462 B.70 C.2 1.463 B.71 C.2 1.464 B.72 C.2 1.465 B.73 C.2 1.466 B.74 C.2 1.467 B.75 C.2 1.468 B.76 C.2 1.469 B.77 C.2 1.470 B.78 C.2 1.471 B.79 C.2 1.472 B.80 C.2 1.473 B.81 C.2 1.474 B.82 C.2 1.475 B.83 C.2 1.476 B.84 C.2 1.477 B.85 C.2 1.478 B.86 C.2 1.479 B.87 C.2 1.480 B.88 C.2 1.481 B.89 C.2 1.482 B.90 C.2 1.483 B.91 C.2 1.484 B.92 C.2 1.485 B.93 C.2 1.486 B.94 C.2 1.487 B.95 C.2 1.488 B.96 C.2 1.489 B.97 C.2 1.490 B.98 C.2 1.491 B.99 C.2 1.492 B.100 C.2 1.493 B.101 C.2 1.494 B.102 C.2 1.495 B.103 C.2 1.496 B.104 C.2 1.497 B.105 C.2 1.498 B.106 C.2 1.499 B.107 C.2 1.500 B.108 C.2 1.501 B.109 C.2 1.502 B.110 C.2 1.503 B.111 C.2 1.504 B.112 C.2 1.505 B.113 C.2 1.506 B.114 C.2 1.507 B.115 C.2 1.508 B.116 C.2 1.509 B.117 C.2 1.510 B.118 C.2 1.511 B.119 C.2 1.512 B.120 C.2 1.513 B.121 C.2 1.514 B.122 C.2 1.515 B.123 C.2 1.516 B.124 C.2 1.517 B.125 C.2 1.518 B.126 C.2 1.519 B.127 C.2 1.520 B.128 C.2 1.521 B.129 C.2 1.522 B.130 C.2 1.523 B.131 C.2 1.524 B.132 C.2 1.525 B.133 C.2 1.526 B.134 C.2 1.527 B.135 C.2 1.528 B.136 C.2 1.529 B.137 C.2 1.530 B.138 C.2 1.531 B.139 C.2 1.532 B.140 C.2 1.533 B.141 C.2 1.534 B.142 C.2 1.535 B.143 C.2 1.536 B.144 C.2 1.537 B.145 C.2 1.538 B.146 C.2 1.539 B.147 C.2 1.540 B.148 C.2 1.541 B.149 C.2 1.542 B.150 C.2 1.543 B.151 C.2 1.544 B.152 C.2 1.545 B.153 C.2 1.546 B.154 C.2 1.547 B.155 C.2 1.548 B.156 C.2 1.549 B.157 C.2 1.550 B.158 C.2 1.551 B.159 C.2 1.552 B.160 C.2 1.553 B.161 C.2 1.554 B.162 C.2 1.555 B.163 C.2 1.556 B.164 C.2 1.557 B.165 C.2 1.558 B.166 C.2 1.559 B.167 C.2 1.560 B.168 C.2 1.561 B.169 C.2 1.562 B.170 C.2 1.563 B.171 C.2 1.564 B.172 C.2 1.565 B.173 C.2 1.566 B.174 C.2 1.567 B.175 C.2 1.568 B.176 C.2 1.569 B.177 C.2 1.570 B.178 C.2 1.571 B.179 C.2 1.572 B.180 C.2 1.573 B.181 C.2 1.574 B.182 C.2 1.575 B.183 C.2 1.576 B.184 C.2 1.577 B.185 C.2 1.578 B.186 C.2 1.579 B.187 C.2 1.580 B.188 C.2 1.581 B.189 C.2 1.582 B.190 C.2 1.583 B.191 C.2 1.584 B.192 C.2 1.585 B.193 C.2 1.586 B.194 C.2 1.587 B.195 C.2 1.588 B.196 C.2 1.589 B.1 C.3 1.590 B.2 C.3 1.591 B.3 C.3 1.592 B.4 C.3 1.593 B.5 C.3 1.594 B.6 C.3 1.595 B.7 C.3 1.596 B.8 C.3 1.597 B.9 C.3 1.598 B.10 C.3 1.599 B.11 C.3 1.600 B.12 C.3 1.601 B.13 C.3 1.602 B.14 C.3 1.603 B.15 C.3 1.604 B.16 C.3 1.605 B.17 C.3 1.606 B.18 C.3 1.607 B.19 C.3 1.608 B.20 C.3 1.609 B.21 C.3 1.610 B.22 C.3 1.611 B.23 C.3 1.612 B.24 C.3 1.613 B.25 C.3 1.614 B.26 C.3 1.615 B.27 C.3 1.616 B.28 C.3 1.617 B.29 C.3 1.618 B.30 C.3 1.619 B.31 C.3 1.620 B.32 C.3 1.621 B.33 C.3 1.622 B.34 C.3 1.623 B.35 C.3 1.624 B.36 C.3 1.625 B.37 C.3 1.626 B.38 C.3 1.627 B.39 C.3 1.628 B.40 C.3 1.629 B.41 C.3 1.630 B.42 C.3 1.631 B.43 C.3 1.632 B.44 C.3 1.633 B.45 C.3 1.634 B.46 C.3 1.635 B.47 C.3 1.636 B.48 C.3 1.637 B.49 C.3 1.638 B.50 C.3 1.639 B.51 C.3 1.640 B.52 C.3 1.641 B.53 C.3 1.642 B.54 C.3 1.643 B.55 C.3 1.644 B.56 C.3 1.645 B.57 C.3 1.646 B.58. C.3 1.647 B.59 C.3 1.648 B.60 C.3 1.649 B.61 C.3 1.650 B.62 C.3 1.651 B.63 C.3 1.652 B.64 C.3 1.653 B.65 C.3 1.654 B.66 C.3 1.655 B.67 C.3 1.656 B.68 C.3 1.657 B.69 C.3 1.658 B.70 C.3 1.659 B.71 C.3 1.660 B.72 C.3 1.661 B.73 C.3 1.662 B.74 C.3 1.663 B.75 C.3 1.664 B.76 C.3 1.665 B.77 C.3 1.666 B.78 C.3 1.667 B.79 C.3 1.668 B.80 C.3 1.669 B.81 C.3 1.670 B.82 C.3 1.671 B.83 C.3 1.672 B.84 C.3 1.673 B.85 C.3 1.674 B.86 C.3 1.675 B.87 C.3 1.676 B.88 C.3 1.677 B.89 C.3 1.678 B.90 C.3 1.679 B.91 C.3 1.680 B.92 C.3 1.681 B.93 C.3 1.682 B.94 C.3 1.683 B.95 C.3 1.684 B.96 C.3 1.685 B.97 C.3 1.686 B.98 C.3 1.687 B.99 C.3 1.688 B.100 C.3 1.689 B.101 C.3 1.690 B.102 C.3 1.691 B.103 C.3 1.692 B.104 C.3 1.693 B.105 C.3 1.694 B.106 C.3 1.695 B.107 C.3 1.696 B.108 C.3 1.697 B.109 C.3 1.698 B.110 C.3 1.699 B.111 C.3 1.700 B.112 C.3 1.701 B.113 C.3 1.702 B.114 C.3 1.703 B.115 C.3 1.704 B.116 C.3 1.705 B.117 C.3 1.706 B.118 C.3 1.707 B.119 C.3 1.708 B.120 C.3 1.709 B.121 C.3 1.710 B.122 C.3 1.711 B.123 C.3 1.712 B.124 C.3 1.713 B.125 C.3 1.714 B.126 C.3 1.715 B.127 C.3 1.716 B.128 C.3 1.717 B.129 C.3 1.718 B.130 C.3 1.719 B.131 C.3 1.720 B.132 C.3 1.721 B.133 C.3 1.722 B.134 C.3 1.723 B.135 C.3 1.724 B.136 C.3 1.725 B.137 C.3 1.726 B.138 C.3 1.727 B.139 C.3 1.728 B.140 C.3 1.729 B.141 C.3 1.730 B.142 C.3 1.731 B.143 C.3 1.732 B.144 C.3 1.733 B.145 C.3 1.734 B.146 C.3 1.735 B.147 C.3 1.736 B.148 C.3 1.737 B.149 C.3 1.738 B.150 C.3 1.739 B.151 C.3 1.740 B.152 C.3 1.741 B.153 C.3 1.742 B.154 C.3 1.743 B.155 C.3 1.744 B.156 C.3 1.745 B.157 C.3 1.746 B.158 C.3 1.747 B.159 C.3 1.748 B.160 C.3 1.749 B.161 C.3 1.750 B.162 C.3 1.751 B.163 C.3 1.752 B.164 C.3 1.753 B.165 C.3 1.754 B.166 C.3 1.755 B.167 C.3 1.756 B.168 C.3 1.757 B.169 C.3 1.758 B.170 C.3 1.759 B.171 C.3 1.760 B.172 C.3 1.761 B.173 C.3 1.762 B.174 C.3 1.763 B.175 C.3 1.764 B.176 C.3 1.765 B.177 C.3 1.766 B.178 C.3 1.767 B.179 C.3 1.768 B.180 C.3 1.769 B.181 C.3 1.770 B.182 C.3 1.771 B.183 C.3 1.772 B.184 C.3 1.773 B.185 C.3 1.774 B.186 C.3 1.775 B.187 C.3 1.776 B.188 C.3 1.777 B.189 C.3 1.778 B.190 C.3 1.779 B.191 C.3 1.780 B.192 C.3 1.781 B.193 C.3 1.782 B.194 C.3 1.783 B.195 C.3 1.784 B.196 C.3 1.785 B.1 C.4 1.786 B.2 C.4 1.787 B.3 C.4 1.788 B.4 C.4 1.789 B.5 C.4 1.790 B.6 C.4 1.791 B.7 C.4 1.792 B.8 C.4 1.793 B.9 C.4 1.794 B.10 C.4 1.795 B.11 C.4 1.796 B.12 C.4 1.797 B.13 C.4 1.798 B.14 C.4 1.799 B.15 C.4 1.800 B.16 C.4 1.801 B.17 C.4 1.802 B.18 C.4 1.803 B.19 C.4 1.804 B.20 C.4 1.805 B.21 C.4 1.806 B.22 C.4 1.807 B.23 C.4 1.808 B.24 C.4 1.809 B.25 C.4 1.810 B.26 C.4 1.811 B.27 C.4 1.812 B.28 C.4 1.813 B.29 C.4 1.814 B.30 C.4 1.815 B.31 C.4 1.816 B.32 C.4 1.817 B.33 C.4 1.818 B.34 C.4 1.819 B.35 C.4 1.820 B.36 C.4 1.821 B.37 C.4 1.822 B.38 C.4 1.823 B.39 C.4 1.824 B.40 C.4 1.825 B.41 C.4 1.826 B.42 C.4 1.827 B.43 C.4 1.828 B.44 C.4 1.829 B.45 C.4 1.830 B.46 C.4 1.831 B.47 C.4 1.832 B.48 C.4 1.833 B.49 C.4 1.834 B.50 C.4 1.835 B.51 C.4 1.836 B.52 C.4 1.837 B.53 C.4 1.838 B.54 C.4 1.839 B.55 C.4 1.840 B.56 C.4 1.841 B.57 C.4 1.842 B.58. C.4 1.843 B.59 C.4 1.844 B.60 C.4 1.845 B.61 C.4 1.846 B.62 C.4 1.847 B.63 C.4 1.848 B.64 C.4 1.849 B.65 C.4 1.850 B.66 C.4 1.851 B.67 C.4 1.852 B.68 C.4 1.853 B.69 C.4 1.854 B.70 C.4 1.855 B.71 C.4 1.856 B.72 C.4 1.857 B.73 C.4 1.858 B.74 C.4 1.859 B.75 C.4 1.860 B.76 C.4 1.861 B.77 C.4 1.862 B.78 C.4 1.863 B.79 C.4 1.864 B.80 C.4 1.865 B.81 C.4 1.866 B.82 C.4 1.867 B.83 C.4 1.868 B.84 C.4 1.869 B.85 C.4 1.870 B.86 C.4 1.871 B.87 C.4 1.872 B.88 C.4 1.873 B.89 C.4 1.874 B.90 C.4 1.875 B.91 C.4 1.876 B.92 C.4 1.877 B.93 C.4 1.878 B.94 C.4 1.879 B.95 C.4 1.880 B.96 C.4 1.881 B.97 C.4 1.882 B.98 C.4 1.883 B.99 C.4 1.884 B.100 C.4 1.885 B.101 C.4 1.886 B.102 C.4 1.887 B.103 C.4 1.888 B.104 C.4 1.889 B.105 C.4 1.890 B.106 C.4 1.891 B.107 C.4 1.892 B.108 C.4 1.893 B.109 C.4 1.894 B.110 C.4 1.895 B.111 C.4 1.896 B.112 C.4 1.897 B.113 C.4 1.898 B.114 C.4 1.899 B.115 C.4 1.900 B.116 C.4 1.901 B.117 C.4 1.902 B.118 C.4 1.903 B.119 C.4 1.904 B.120 C.4 1.905 B.121 C.4 1.906 B.122 C.4 1.907 B.123 C.4 1.908 B.124 C.4 1.909 B.125 C.4 1.910 B.126 C.4 1.911 B.127 C.4 1.912 B.128 C.4 1.913 B.129 C.4 1.914 B.130 C.4 1.915 B.131 C.4 1.916 B.132 C.4 1.917 B.133 C.4 1.918 B.134 C.4 1.919 B.135 C.4 1.920 B.136 C.4 1.921 B.137 C.4 1.922 B.138 C.4 1.923 B.139 C.4 1.924 B.140 C.4 1.925 B.141 C.4 1.926 B.142 C.4 1.927 B.143 C.4 1.928 B.144 C.4 1.929 B.145 C.4 1.930 B.146 C.4 1.931 B.147 C.4 1.932 B.148 C.4 1.933 B.149 C.4 1.934 B.150 C.4 1.935 B.151 C.4 1.936 B.152 C.4 1.937 B.153 C.4 1.938 B.154 C.4 1.939 B.155 C.4 1.940 B.156 C.4 1.941 B.157 C.4 1.942 B.158 C.4 1.943 B.159 C.4 1.944 B.160 C.4 1.945 B.161 C.4 1.946 B.162 C.4 1.947 B.163 C.4 1.948 B.164 C.4 1.949 B.165 C.4 1.950 B.166 C.4 1.951 B.167 C.4 1.952 B.168 C.4 1.953 B.169 C.4 1.954 B.170 C.4 1.955 B.171 C.4 1.956 B.172 C.4 1.957 B.173 C.4 1.958 B.174 C.4 1.959 B.175 C.4 1.960 B.176 C.4 1.961 B.177 C.4 1.962 B.178 C.4 1.963 B.179 C.4 1.964 B.180 C.4 1.965 B.181 C.4 1.966 B.182 C.4 1.967 B.183 C.4 1.968 B.184 C.4 1.969 B.185 C.4 1.970 B.186 C.4 1.971 B.187 C.4 1.972 B.188 C.4 1.973 B.189 C.4 1.974 B.190 C.4 1.975 B.191 C.4 1.976 B.192 C.4 1.977 B.193 C.4 1.978 B.194 C.4 1.979 B.195 C.4 1.980 B.196 C.4 1.981 B.1 C.5 1.982 B.2 C.5 1.983 B.3 C.5 1.984 B.4 C.5 1.985 B.5 C.5 1.986 B.6 C.5 1.987 B.7 C.5 1.988 B.8 C.5 1.989 B.9 C.5 1.990 B.10 C.5 1.991 B.11 C.5 1.992 B.12 C.5 1.993 B.13 C.5 1.994 B.14 C.5 1.995 B.15 C.5 1.996 B.16 C.5 1.997 B.17 C.5 1.998 B.18 C.5 1.999 B.19 C.5 1.1000 B.20 C.5 1.1001 B.21 C.5 1.1002 B.22 C.5 1.1003 B.23 C.5 1.1004 B.24 C.5 1.1005 B.25 C.5 1.1006 B.26 C.5 1.1007 B.27 C.5 1.1008 B.28 C.5 1.1009 B.29 C.5 1.1010 B.30 C.5 1.1011 B.31 C.5 1.1012 B.32 C.5 1.1013 B.33 C.5 1.1014 B.34 C.5 1.1015 B.35 C.5 1.1016 B.36 C.5 1.1017 B.37 C.5 1.1018 B.38 C.5 1.1019 B.39 C.5 1.1020 B.40 C.5 1.1021 B.41 C.5 1.1022 B.42 C.5 1.1023 B.43 C.5 1.1024 B.44 C.5 1.1025 B.45 C.5 1.1026 B.46 C.5 1.1027 B.47 C.5 1.1028 B.48 C.5 1.1029 B.49 C.5 1.1030 B.50 C.5 1.1031 B.51 C.5 1.1032 B.52 C.5 1.1033 B.53 C.5 1.1034 B.54 C.5 1.1035 B.55 C.5 1.1036 B.56 C.5 1.1037 B.57 C.5 1.1038 B.58. C.5 1.1039 B.59 C.5 1.1040 B.60 C.5 1.1041 B.61 C.5 1.1042 B.62 C.5 1.1043 B.63 C.5 1.1044 B.64 C.5 1.1045 B.65 C.5 1.1046 B.66 C.5 1.1047 B.67 C.5 1.1048 B.68 C.5 1.1049 B.69 C.5 1.1050 B.70 C.5 1.1051 B.71 C.5 1.1052 B.72 C.5 1.1053 B.73 C.5 1.1054 B.74 C.5 1.1055 B.75 C.5 1.1056 B.76 C.5 1.1057 B.77 C.5 1.1058 B.78 C.5 1.1059 B.79 C.5 1.1060 B.80 C.5 1.1061 B.81 C.5 1.1062 B.82 C.5 1.1063 B.83 C.5 1.1064 B.84 C.5 1.1065 B.85 C.5 1.1066 B.86 C.5 1.1067 B.87 C.5 1.1068 B.88 C.5 1.1069 B.89 C.5 1.1070 B.90 C.5 1.1071 B.91 C.5 1.1072 B.92 C.5 1.1073 B.93 C.5 1.1074 B.94 C.5 1.1075 B.95 C.5 1.1076 B.96 C.5 1.1077 B.97 C.5 1.1078 B.98 C.5 1.1079 B.99 C.5 1.1080 B.100 C.5 1.1081 B.101 C.5 1.1082 B.102 C.5 1.1083 B.103 C.5 1.1084 B.104 C.5 1.1085 B.105 C.5 1.1086 B.106 C.5 1.1087 B.107 C.5 1.1088 B.108 C.5 1.1089 B.109 C.5 1.1090 B.110 C.5 1.1091 B.111 C.5 1.1092 B.112 C.5 1.1093 B.113 C.5 1.1094 B.114 C.5 1.1095 B.115 C.5 1.1096 B.116 C.5 1.1097 B.117 C.5 1.1098 B.118 C.5 1.1099 B.119 C.5 1.1100 B.120 C.5 1.1101 B.121 C.5 1.1102 B.122 C.5 1.1103 B.123 C.5 1.1104 B.124 C.5 1.1105 B.125 C.5 1.1106 B.126 C.5 1.1107 B.127 C.5 1.1108 B.128 C.5 1.1109 B.129 C.5 1.1110 B.130 C.5 1.1111 B.131 C.5 1.1112 B.132 C.5 1.1113 B.133 C.5 1.1114 B.134 C.5 1.1115 B.135 C.5 1.1116 B.136 C.5 1.1117 B.137 C.5 1.1118 B.138 C.5 1.1119 B.139 C.5 1.1120 B.140 C.5 1.1121 B.141 C.5 1.1122 B.142 C.5 1.1123 B.143 C.5 1.1124 B.144 C.5 1.1125 B.145 C.5 1.1126 B.146 C.5 1.1127 B.147 C.5 1.1128 B.148 C.5 1.1129 B.149 C.5 1.1130 B.150 C.5 1.1131 B.151 C.5 1.1132 B.152 C.5 1.1133 B.153 C.5 1.1134 B.154 C.5 1.1135 B.155 C.5 1.1136 B.156 C.5 1.1137 B.157 C.5 1.1138 B.158 C.5 1.1139 B.159 C.5 1.1140 B.160 C.5 1.1141 B.161 C.5 1.1142 B.162 C.5 1.1143 B.163 C.5 1.1144 B.164 C.5 1.1145 B.165 C.5 1.1146 B.166 C.5 1.1147 B.167 C.5 1.1148 B.168 C.5 1.1149 B.169 C.5 1.1150 B.170 C.5 1.1151 B.171 C.5 1.1152 B.172 C.5 1.1153 B.173 C.5 1.1154 B.174 C.5 1.1155 B.175 C.5 1.1156 B.176 C.5 1.1157 B.177 C.5 1.1158 B.178 C.5 1.1159 B.179 C.5 1.1160 B.180 C.5 1.1161 B.181 C.5 1.1162 B.182 C.5 1.1163 B.183 C.5 1.1164 B.184 C.5 1.1165 B.185 C.5 1.1166 B.186 C.5 1.1167 B.187 C.5 1.1168 B.188 C.5 1.1169 B.189 C.5 1.1170 B.190 C.5 1.1171 B.191 C.5 1.1172 B.192 C.5 1.1173 B.193 C.5 1.1174 B.194 C.5 1.1175 B.195 C.5 1.1176 B.196 C.5 1.1177 B.1 C.6 1.1178 B.2 C.6 1.1179 B.3 C.6 1.1180 B.4 C.6 1.1181 B.5 C.6 1.1182 B.6 C.6 1.1183 B.7 C.6 1.1184 B.8 C.6 1.1185 B.9 C.6 1.1186 B.10 C.6 1.1187 B.11 C.6 1.1188 B.12 C.6 1.1189 B.13 C.6 1.1190 B.14 C.6 1.1191 B.15 C.6 1.1192 B.16 C.6 1.1193 B.17 C.6 1.1194 B.18 C.6 1.1195 B.19 C.6 1.1196 B.20 C.6 1.1197 B.21 C.6 1.1198 B.22 C.6 1.1199 B.23 C.6 1.1200 B.24 C.6 1.1201 B.25 C.6 1.1202 B.26 C.6 1.1203 B.27 C.6 1.1204 B.28 C.6 1.1205 B.29 C.6 1.1206 B.30 C.6 1.1207 B.31 C.6 1.1208 B.32 C.6 1.1209 B.33 C.6 1.1210 B.34 C.6 1.1211 B.35 C.6 1.1212 B.36 C.6 1.1213 B.37 C.6 1.1214 B.38 C.6 1.1215 B.39 C.6 1.1216 B.40 C.6 1.1217 B.41 C.6 1.1218 B.42 C.6 1.1219 B.43 C.6 1.1220 B.44 C.6 1.1221 B.45 C.6 1.1222 B.46 C.6 1.1223 B.47 C.6 1.1224 B.48 C.6 1.1225 B.49 C.6 1.1226 B.50 C.6 1.1227 B.51 C.6 1.1228 B.52 C.6 1.1229 B.53 C.6 1.1230 B.54 C.6 1.1231 B.55 C.6 1.1232 B.56 C.6 1.1233 B.57 C.6 1.1234 B.58. C.6 1.1235 B.59 C.6 1.1236 B.60 C.6 1.1237 B.61 C.6 1.1238 B.62 C.6 1.1239 B.63 C.6 1.1240 B.64 C.6 1.1241 B.65 C.6 1.1242 B.66 C.6 1.1243 B.67 C.6 1.1244 B.68 C.6 1.1245 B.69 C.6 1.1246 B.70 C.6 1.1247 B.71 C.6 1.1248 B.72 C.6 1.1249 B.73 C.6 1.1250 B.74 C.6 1.1251 B.75 C.6 1.1252 B.76 C.6 1.1253 B.77 C.6 1.1254 B.78 C.6 1.1255 B.79 C.6 1.1256 B.80 C.6 1.1257 B.81 C.6 1.1258 B.82 C.6 1.1259 B.83 C.6 1.1260 B.84 C.6 1.1261 B.85 C.6 1.1262 B.86 C.6 1.1263 B.87 C.6 1.1264 B.88 C.6 1.1265 B.89 C.6 1.1266 B.90 C.6 1.1267 B.91 C.6 1.1268 B.92 C.6 1.1269 B.93 C.6 1.1270 B.94 C.6 1.1271 B.95 C.6 1.1272 B.96 C.6 1.1273 B.97 C.6 1.1274 B.98 C.6 1.1275 B.99 C.6 1.1276 B.100 C.6 1.1277 B.101 C.6 1.1278 B.102 C.6 1.1279 B.103 C.6 1.1280 B.104 C.6 1.1281 B.105 C.6 1.1282 B.106 C.6 1.1283 B.107 C.6 1.1284 B.108 C.6 1.1285 B.109 C.6 1.1286 B.110 C.6 1.1287 B.111 C.6 1.1288 B.112 C.6 1.1289 B.113 C.6 1.1290 B.114 C.6 1.1291 B.115 C.6 1.1292 B.116 C.6 1.1293 B.117 C.6 1.1294 B.118 C.6 1.1295 B.119 C.6 1.1296 B.120 C.6 1.1297 B.121 C.6 1.1298 B.122 C.6 1.1299 B.123 C.6 1.1300 B.124 C.6 1.1301 B.125 C.6 1.1302 B.126 C.6 1.1303 B.127 C.6 1.1304 B.128 C.6 1.1305 B.129 C.6 1.1306 B.130 C.6 1.1307 B.131 C.6 1.1308 B.132 C.6 1.1309 B.133 C.6 1.1310 B.134 C.6 1.1311 B.135 C.6 1.1312 B.136 C.6 1.1313 B.137 C.6 1.1314 B.138 C.6 1.1315 B.139 C.6 1.1316 B.140 C.6 1.1317 B.141 C.6 1.1318 B.142 C.6 1.1319 B.143 C.6 1.1320 B.144 C.6 1.1321 B.145 C.6 1.1322 B.146 C.6 1.1323 B.147 C.6 1.1324 B.148 C.6 1.1325 B.149 C.6 1.1326 B.150 C.6 1.1327 B.151 C.6 1.1328 B.152 C.6 1.1329 B.153 C.6 1.1330 B.154 C.6 1.1331 B.155 C.6 1.1332 B.156 C.6 1.1333 B.157 C.6 1.1334 B.158 C.6 1.1335 B.159 C.6 1.1336 B.160 C.6 1.1337 B.161 C.6 1.1338 B.162 C.6 1.1339 B.163 C.6 1.1340 B.164 C.6 1.1341 B.165 C.6 1.1342 B.166 C.6 1.1343 B.167 C.6 1.1344 B.168 C.6 1.1345 B.169 C.6 1.1346 B.170 C.6 1.1347 B.171 C.6 1.1348 B.172 C.6 1.1349 B.173 C.6 1.1350 B.174 C.6 1.1351 B.175 C.6 1.1352 B.176 C.6 1.1353 B.177 C.6 1.1354 B.178 C.6 1.1355 B.179 C.6 1.1356 B.180 C.6 1.1357 B.181 C.6 1.1358 B.182 C.6 1.1359 B.183 C.6 1.1360 B.184 C.6 1.1361 B.185 C.6 1.1362 B.186 C.6 1.1363 B.187 C.6 1.1364 B.188 C.6 1.1365 B.189 C.6 1.1366 B.190 C.6 1.1367 B.191 C.6 1.1368 B.192 C.6 1.1369 B.193 C.6 1.1370 B.194 C.6 1.1371 B.195 C.6 1.1372 B.196 C.6 1.1373 B.1 C.7 1.1374 B.2 C.7 1.1375 B.3 C.7 1.1376 B.4 C.7 1.1377 B.5 C.7 1.1378 B.6 C.7 1.1379 B.7 C.7 1.1380 B.8 C.7 1.1381 B.9 C.7 1.1382 B.10 C.7 1.1383 B.11 C.7 1.1384 B.12 C.7 1.1385 B.13 C.7 1.1386 B.14 C.7 1.1387 B.15 C.7 1.1388 B.16 C.7 1.1389 B.17 C.7 1.1390 B.18 C.7 1.1391 B.19 C.7 1.1392 B.20 C.7 1.1393 B.21 C.7 1.1394 B.22 C.7 1.1395 B.23 C.7 1.1396 B.24 C.7 1.1397 B.25 C.7 1.1398 B.26 C.7 1.1399 B.27 C.7 1.1400 B.28 C.7 1.1401 B.29 C.7 1.1402 B.30 C.7 1.1403 B.31 C.7 1.1404 B.32 C.7 1.1405 B.33 C.7 1.1406 B.34 C.7 1.1407 B.35 C.7 1.1408 B.36 C.7 1.1409 B.37 C.7 1.1410 B.38 C.7 1.1411 B.39 C.7 1.1412 B.40 C.7 1.1413 B.41 C.7 1.1414 B.42 C.7 1.1415 B.43 C.7 1.1416 B.44 C.7 1.1417 B.45 C.7 1.1418 B.46 C.7 1.1419 B.47 C.7 1.1420 B.48 C.7 1.1421 B.49 C.7 1.1422 B.50 C.7 1.1423 B.51 C.7 1.1424 B.52 C.7 1.1425 B.53 C.7 1.1426 B.54 C.7 1.1427 B.55 C.7 1.1428 B.56 C.7 1.1429 B.57 C.7 1.1430 B.58. C.7 1.1431 B.59 C.7 1.1432 B.60 C.7 1.1433 B.61 C.7 1.1434 B.62 C.7 1.1435 B.63 C.7 1.1436 B.64 C.7 1.1437 B.65 C.7 1.1438 B.66 C.7 1.1439 B.67 C.7 1.1440 B.68 C.7 1.1441 B.69 C.7 1.1442 B.70 C.7 1.1443 B.71 C.7 1.1444 B.72 C.7 1.1445 B.73 C.7 1.1446 B.74 C.7 1.1447 B.75 C.7 1.1448 B.76 C.7 1.1449 B.77 C.7 1.1450 B.78 C.7 1.1451 B.79 C.7 1.1452 B.80 C.7 1.1453 B.81 C.7 1.1454 B.82 C.7 1.1455 B.83 C.7 1.1456 B.84 C.7 1.1457 B.85 C.7 1.1458 B.86 C.7 1.1459 B.87 C.7 1.1460 B.88 C.7 1.1461 B.89 C.7 1.1462 B.90 C.7 1.1463 B.91 C.7 1.1464 B.92 C.7 1.1465 B.93 C.7 1.1466 B.94 C.7 1.1467 B.95 C.7 1.1468 B.96 C.7 1.1469 B.97 C.7 1.1470 B.98 C.7 1.1471 B.99 C.7 1.1472 B.100 C.7 1.1473 B.101 C.7 1.1474 B.102 C.7 1.1475 B.103 C.7 1.1476 B.104 C.7 1.1477 B.105 C.7 1.1478 B.106 C.7 1.1479 B.107 C.7 1.1480 B.108 C.7 1.1481 B.109 C.7 1.1482 B.110 C.7 1.1483 B.111 C.7 1.1484 B.112 C.7 1.1485 B.113 C.7 1.1486 B.114 C.7 1.1487 B.115 C.7 1.1488 B.116 C.7 1.1489 B.117 C.7 1.1490 B.118 C.7 1.1491 B.119 C.7 1.1492 B.120 C.7 1.1493 B.121 C.7 1.1494 B.122 C.7 1.1495 B.123 C.7 1.1496 B.124 C.7 1.1497 B.125 C.7 1.1498 B.126 C.7 1.1499 B.127 C.7 1.1500 B.128 C.7 1.1501 B.129 C.7 1.1502 B.130 C.7 1.1503 B.131 C.7 1.1504 B.132 C.7 1.1505 B.133 C.7 1.1506 B.134 C.7 1.1507 B.135 C.7 1.1508 B.136 C.7 1.1509 B.137 C.7 1.1510 B.138 C.7 1.1511 B.139 C.7 1.1512 B.140 C.7 1.1513 B.141 C.7 1.1514 B.142 C.7 1.1515 B.143 C.7 1.1516 B.144 C.7 1.1517 B.145 C.7 1.1518 B.146 C.7 1.1519 B.147 C.7 1.1520 B.148 C.7 1.1521 B.149 C.7 1.1522 B.150 C.7 1.1523 B.151 C.7 1.1524 B.152 C.7 1.1525 B.153 C.7 1.1526 B.154 C.7 1.1527 B.155 C.7 1.1528 B.156 C.7 1.1529 B.157 C.7 1.1530 B.158 C.7 1.1531 B.159 C.7 1.1532 B.160 C.7 1.1533 B.161 C.7 1.1534 B.162 C.7 1.1535 B.163 C.7 1.1536 B.164 C.7 1.1537 B.165 C.7 1.1538 B.166 C.7 1.1539 B.167 C.7 1.1540 B.168 C.7 1.1541 B.169 C.7 1.1542 B.170 C.7 1.1543 B.171 C.7 1.1544 B.172 C.7 1.1545 B.173 C.7 1.1546 B.174 C.7 1.1547 B.175 C.7 1.1548 B.176 C.7 1.1549 B.177 C.7 1.1550 B.178 C.7 1.1551 B.179 C.7 1.1552 B.180 C.7 1.1553 B.181 C.7 1.1554 B.182 C.7 1.1555 B.183 C.7 1.1556 B.184 C.7 1.1557 B.185 C.7 1.1558 B.186 C.7 1.1559 B.187 C.7 1.1560 B.188 C.7 1.1561 B.189 C.7 1.1562 B.190 C.7 1.1563 B.191 C.7 1.1564 B.192 C.7 1.1565 B.193 C.7 1.1566 B.194 C.7 1.1567 B.195 C.7 1.1568 B.196 C.7 1.1569 B.1 C.8 1.1570 B.2 C.8 1.1571 B.3 C.8 1.1572 B.4 C.8 1.1573 B.5 C.8 1.1574 B.6 C.8 1.1575 B.7 C.8 1.1576 B.8 C.8 1.1577 B.9 C.8 1.1578 B.10 C.8 1.1579 B.11 C.8 1.1580 B.12 C.8 1.1581 B.13 C.8 1.1582 B.14 C.8 1.1583 B.15 C.8 1.1584 B.16 C.8 1.1585 B.17 C.8 1.1586 B.18 C.8 1.1587 B.19 C.8 1.1588 B.20 C.8 1.1589 B.21 C.8 1.1590 B.22 C.8 1.1591 B.23 C.8 1.1592 B.24 C.8 1.1593 B.25 C.8 1.1594 B.26 C.8 1.1595 B.27 C.8 1.1596 B.28 C.8 1.1597 B.29 C.8 1.1598 B.30 C.8 1.1599 B.31 C.8 1.1600 B.32 C.8 1.1601 B.33 C.8 1.1602 B.34 C.8 1.1603 B.35 C.8 1.1604 B.36 C.8 1.1605 B.37 C.8 1.1606 B.38 C.8 1.1607 B.39 C.8 1.1608 B.40 C.8 1.1609 B.41 C.8 1.1610 B.42 C.8 1.1611 B.43 C.8 1.1612 B.44 C.8 1.1613 B.45 C.8 1.1614 B.46 C.8 1.1615 B.47 C.8 1.1616 B.48 C.8 1.1617 B.49 C.8 1.1618 B.50 C.8 1.1619 B.51 C.8 1.1620 B.52 C.8 1.1621 B.53 C.8 1.1622 B.54 C.8 1.1623 B.55 C.8 1.1624 B.56 C.8 1.1625 B.57 C.8 1.1626 B.58. C.8 1.1627 B.59 C.8 1.1628 B.60 C.8 1.1629 B.61 C.8 1.1630 B.62 C.8 1.1631 B.63 C.8 1.1632 B.64 C.8 1.1633 B.65 C.8 1.1634 B.66 C.8 1.1635 B.67 C.8 1.1636 B.68 C.8 1.1637 B.69 C.8 1.1638 B.70 C.8 1.1639 B.71 C.8 1.1640 B.72 C.8 1.1641 B.73 C.8 1.1642 B.74 C.8 1.1643 B.75 C.8 1.1644 B.76 C.8 1.1645 B.77 C.8 1.1646 B.78 C.8 1.1647 B.79 C.8 1.1648 B.80 C.8 1.1649 B.81 C.8 1.1650 B.82 C.8 1.1651 B.83 C.8 1.1652 B.84 C.8 1.1653 B.85 C.8 1.1654 B.86 C.8 1.1655 B.87 C.8 1.1656 B.88 C.8 1.1657 B.89 C.8 1.1658 B.90 C.8 1.1659 B.91 C.8 1.1660 B.92 C.8 1.1661 B.93 C.8 1.1662 B.94 C.8 1.1663 B.95 C.8 1.1664 B.96 C.8 1.1665 B.97 C.8 1.1666 B.98 C.8 1.1667 B.99 C.8 1.1668 B.100 C.8 1.1669 B.101 C.8 1.1670 B.102 C.8 1.1671 B.103 C.8 1.1672 B.104 C.8 1.1673 B.105 C.8 1.1674 B.106 C.8 1.1675 B.107 C.8 1.1676 B.108 C.8 1.1677 B.109 C.8 1.1678 B.110 C.8 1.1679 B.111 C.8 1.1680 B.112 C.8 1.1681 B.113 C.8 1.1682 B.114 C.8 1.1683 B.115 C.8 1.1684 B.116 C.8 1.1685 B.117 C.8 1.1686 B.118 C.8 1.1687 B.119 C.8 1.1688 B.120 C.8 1.1689 B.121 C.8 1.1690 B.122 C.8 1.1691 B.123 C.8 1.1692 B.124 C.8 1.1693 B.125 C.8 1.1694 B.126 C.8 1.1695 B.127 C.8 1.1696 B.128 C.8 1.1697 B.129 C.8 1.1698 B.130 C.8 1.1699 B.131 C.8 1.1700 B.132 C.8 1.1701 B.133 C.8 1.1702 B.134 C.8 1.1703 B.135 C.8 1.1704 B.136 C.8 1.1705 B.137 C.8 1.1706 B.138 C.8 1.1707 B.139 C.8 1.1708 B.140 C.8 1.1709 B.141 C.8 1.1710 B.142 C.8 1.1711 B.143 C.8 1.1712 B.144 C.8 1.1713 B.145 C.8 1.1714 B.146 C.8 1.1715 B.147 C.8 1.1716 B.148 C.8 1.1717 B.149 C.8 1.1718 B.150 C.8 1.1719 B.151 C.8 1.1720 B.152 C.8 1.1721 B.153 C.8 1.1722 B.154 C.8 1.1723 B.155 C.8 1.1724 B.156 C.8 1.1725 B.157 C.8 1.1726 B.158 C.8 1.1727 B.159 C.8 1.1728 B.160 C.8 1.1729 B.161 C.8 1.1730 B.162 C.8 1.1731 B.163 C.8 1.1732 B.164 C.8 1.1733 B.165 C.8 1.1734 B.166 C.8 1.1735 B.167 C.8 1.1736 B.168 C.8 1.1737 B.169 C.8 1.1738 B.170 C.8 1.1739 B.171 C.8 1.1740 B.172 C.8 1.1741 B.173 C.8 1.1742 B.174 C.8 1.1743 B.175 C.8 1.1744 B.176 C.8 1.1745 B.177 C.8 1.1746 B.178 C.8 1.1747 B.179 C.8 1.1748 B.180 C.8 1.1749 B.181 C.8 1.1750 B.182 C.8 1.1751 B.183 C.8 1.1752 B.184 C.8 1.1753 B.185 C.8 1.1754 B.186 C.8 1.1755 B.187 C.8 1.1756 B.188 C.8 1.1757 B.189 C.8 1.1758 B.190 C.8 1.1759 B.191 C.8 1.1760 B.192 C.8 1.1761 B.193 C.8 1.1762 B.194 C.8 1.1763 B.195 C.8 1.1764 B.196 C.8 1.1765 B.1 C.9 1.1766 B.2 C.9 1.1767 B.3 C.9 1.1768 B.4 C.9 1.1769 B.5 C.9 1.1770 B.6 C.9 1.1771 B.7 C.9 1.1772 B.8 C.9 1.1773 B.9 C.9 1.1774 B.10 C.9 1.1775 B.11 C.9 1.1776 B.12 C.9 1.1777 B.13 C.9 1.1778 B.14 C.9 1.1779 B.15 C.9 1.1780 B.16 C.9 1.1781 B.17 C.9 1.1782 B.18 C.9 1.1783 B.19 C.9 1.1784 B.20 C.9 1.1785 B.21 C.9 1.1786 B.22 C.9 1.1787 B.23 C.9 1.1788 B.24 C.9 1.1789 B.25 C.9 1.1790 B.26 C.9 1.1791 B.27 C.9 1.1792 B.28 C.9 1.1793 B.29 C.9 1.1794 B.30 C.9 1.1795 B.31 C.9 1.1796 B.32 C.9 1.1797 B.33 C.9 1.1798 B.34 C.9 1.1799 B.35 C.9 1.1800 B.36 C.9 1.1801 B.37 C.9 1.1802 B.38 C.9 1.1803 B.39 C.9 1.1804 B.40 C.9 1.1805 B.41 C.9 1.1806 B.42 C.9 1.1807 B.43 C.9 1.1808 B.44 C.9 1.1809 B.45 C.9 1.1810 B.46 C.9 1.1811 B.47 C.9 1.1812 B.48 C.9 1.1813 B.49 C.9 1.1814 B.50 C.9 1.1815 B.51 C.9 1.1816 B.52 C.9 1.1817 B.53 C.9 1.1818 B.54 C.9 1.1819 B.55 C.9 1.1820 B.56 C.9 1.1821 B.57 C.9 1.1822 B.58. C.9 1.1823 B.59 C.9 1.1824 B.60 C.9 1.1825 B.61 C.9 1.1826 B.62 C.9 1.1827 B.63 C.9 1.1828 B.64 C.9 1.1829 B.65 C.9 1.1830 B.66 C.9 1.1831 B.67 C.9 1.1832 B.68 C.9 1.1833 B.69 C.9 1.1834 B.70 C.9 1.1835 B.71 C.9 1.1836 B.72 C.9 1.1837 B.73 C.9 1.1838 B.74 C.9 1.1839 B.75 C.9 1.1840 B.76 C.9 1.1841 B.77 C.9 1.1842 B.78 C.9 1.1843 B.79 C.9 1.1844 B.80 C.9 1.1845 B.81 C.9 1.1846 B.82 C.9 1.1847 B.83 C.9 1.1848 B.84 C.9 1.1849 B.85 C.9 1.1850 B.86 C.9 1.1851 B.87 C.9 1.1852 B.88 C.9 1.1853 B.89 C.9 1.1854 B.90 C.9 1.1855 B.91 C.9 1.1856 B.92 C.9 1.1857 B.93 C.9 1.1858 B.94 C.9 1.1859 B.95 C.9 1.1860 B.96 C.9 1.1861 B.97 C.9 1.1862 B.98 C.9 1.1863 B.99 C.9 1.1864 B.100 C.9 1.1865 B.101 C.9 1.1866 B.102 C.9 1.1867 B.103 C.9 1.1868 B.104 C.9 1.1869 B.105 C.9 1.1870 B.106 C.9 1.1871 B.107 C.9 1.1872 B.108 C.9 1.1873 B.109 C.9 1.1874 B.110 C.9 1.1875 B.111 C.9 1.1876 B.112 C.9 1.1877 B.113 C.9 1.1878 B.114 C.9 1.1879 B.115 C.9 1.1880 B.116 C.9 1.1881 B.117 C.9 1.1882 B.118 C.9 1.1883 B.119 C.9 1.1884 B.120 C.9 1.1885 B.121 C.9 1.1886 B.122 C.9 1.1887 B.123 C.9 1.1888 B.124 C.9 1.1889 B.125 C.9 1.1890 B.126 C.9 1.1891 B.127 C.9 1.1892 B.128 C.9 1.1893 B.129 C.9 1.1894 B.130 C.9 1.1895 B.131 C.9 1.1896 B.132 C.9 1.1897 B.133 C.9 1.1898 B.134 C.9 1.1899 B.135 C.9 1.1900 B.136 C.9 1.1901 B.137 C.9 1.1902 B.138 C.9 1.1903 B.139 C.9 1.1904 B.140 C.9 1.1905 B.141 C.9 1.1906 B.142 C.9 1.1907 B.143 C.9 1.1908 B.144 C.9 1.1909 B.145 C.9 1.1910 B.146 C.9 1.1911 B.147 C.9 1.1912 B.148 C.9 1.1913 B.149 C.9 1.1914 B.150 C.9 1.1915 B.151 C.9 1.1916 B.152 C.9 1.1917 B.153 C.9 1.1918 B.154 C.9 1.1919 B.155 C.9 1.1920 B.156 C.9 1.1921 B.157 C.9 1.1922 B.158 C.9 1.1923 B.159 C.9 1.1924 B.160 C.9 1.1925 B.161 C.9 1.1926 B.162 C.9 1.1927 B.163 C.9 1.1928 B.164 C.9 1.1929 B.165 C.9 1.1930 B.166 C.9 1.1931 B.167 C.9 1.1932 B.168 C.9 1.1933 B.169 C.9 1.1934 B.170 C.9 1.1935 B.171 C.9 1.1936 B.172 C.9 1.1937 B.173 C.9 1.1938 B.174 C.9 1.1939 B.175 C.9 1.1940 B.176 C.9 1.1941 B.177 C.9 1.1942 B.178 C.9 1.1943 B.179 C.9 1.1944 B.180 C.9 1.1945 B.181 C.9 1.1946 B.182 C.9 1.1947 B.183 C.9 1.1948 B.184 C.9 1.1949 B.185 C.9 1.1950 B.186 C.9 1.1951 B.187 C.9 1.1952 B.188 C.9 1.1953 B.189 C.9 1.1954 B.190 C.9 1.1955 B.191 C.9 1.1956 B.192 C.9 1.1957 B.193 C.9 1.1958 B.194 C.9 1.1959 B.195 C.9 1.1960 B.196 C.9 1.1961 B.1 C.10 1.1962 B.2 C.10 1.1963 B.3 C.10 1.1964 B.4 C.10 1.1965 B.5 C.10 1.1966 B.6 C.10 1.1967 B.7 C.10 1.1968 B.8 C.10 1.1969 B.9 C.10 1.1970 B.10 C.10 1.1971 B.11 C.10 1.1972 B.12 C.10 1.1973 B.13 C.10 1.1974 B.14 C.10 1.1975 B.15 C.10 1.1976 B.16 C.10 1.1977 B.17 C.10 1.1978 B.18 C.10 1.1979 B.19 C.10 1.1980 B.20 C.10 1.1981 B.21 C.10 1.1982 B.22 C.10 1.1983 B.23 C.10 1.1984 B.24 C.10 1.1985 B.25 C.10 1.1986 B.26 C.10 1.1987 B.27 C.10 1.1988 B.28 C.10 1.1989 B.29 C.10 1.1990 B.30 C.10 1.1991 B.31 C.10 1.1992 B.32 C.10 1.1993 B.33 C.10 1.1994 B.34 C.10 1.1995 B.35 C.10 1.1996 B.36 C.10 1.1997 B.37 C.10 1.1998 B.38 C.10 1.1999 B.39 C.10 1.2000 B.40 C.10 1.2001 B.41 C.10 1.2002 B.42 C.10 1.2003 B.43 C.10 1.2004 B.44 C.10 1.2005 B.45 C.10 1.2006 B.46 C.10 1.2007 B.47 C.10 1.2008 B.48 C.10 1.2009 B.49 C.10 1.2010 B.50 C.10 1.2011 B.51 C.10 1.2012 B.52 C.10 1.2013 B.53 C.10 1.2014 B.54 C.10 1.2015 B.55 C.10 1.2016 B.56 C.10 1.2017 B.57 C.10 1.2018 B.58. C.10 1.2019 B.59 C.10 1.2020 B.60 C.10 1.2021 B.61 C.10 1.2022 B.62 C.10 1.2023 B.63 C.10 1.2024 B.64 C.10 1.2025 B.65 C.10 1.2026 B.66 C.10 1.2027 B.67 C.10 1.2028 B.68 C.10 1.2029 B.69 C.10 1.2030 B.70 C.10 1.2031 B.71 C.10 1.2032 B.72 C.10 1.2033 B.73 C.10 1.2034 B.74 C.10 1.2035 B.75 C.10 1.2036 B.76 C.10 1.2037 B.77 C.10 1.2038 B.78 C.10 1.2039 B.79 C.10 1.2040 B.80 C.10 1.2041 B.81 C.10 1.2042 B.82 C.10 1.2043 B.83 C.10 1.2044 B.84 C.10 1.2045 B.85 C.10 1.2046 B.86 C.10 1.2047 B.87 C.10 1.2048 B.88 C.10 1.2049 B.89 C.10 1.2050 B.90 C.10 1.2051 B.91 C.10 1.2052 B.92 C.10 1.2053 B.93 C.10 1.2054 B.94 C.10 1.2055 B.95 C.10 1.2056 B.96 C.10 1.2057 B.97 C.10 1.2058 B.98 C.10 1.2059 B.99 C.10 1.2060 B.100 C.10 1.2061 B.101 C.10 1.2062 B.102 C.10 1.2063 B.103 C.10 1.2064 B.104 C.10 1.2065 B.105 C.10 1.2066 B.106 C.10 1.2067 B.107 C.10 1.2068 B.108 C.10 1.2069 B.109 C.10 1.2070 B.110 C.10 1.2071 B.111 C.10 1.2072 B.112 C.10 1.2073 B.113 C.10 1.2074 B.114 C.10 1.2075 B.115 C.10 1.2076 B.116 C.10 1.2077 B.117 C.10 1.2078 B.118 C.10 1.2079 B.119 C.10 1.2080 B.120 C.10 1.2081 B.121 C.10 1.2082 B.122 C.10 1.2083 B.123 C.10 1.2084 B.124 C.10 1.2085 B.125 C.10 1.2086 B.126 C.10 1.2087 B.127 C.10 1.2088 B.128 C.10 1.2089 B.129 C.10 1.2090 B.130 C.10 1.2091 B.131 C.10 1.2092 B.132 C.10 1.2093 B.133 C.10 1.2094 B.134 C.10 1.2095 B.135 C.10 1.2096 B.136 C.10 1.2097 B.137 C.10 1.2098 B.138 C.10 1.2099 B.139 C.10 1.2100 B.140 C.10 1.2101 B.141 C.10 1.2102 B.142 C.10 1.2103 B.143 C.10 1.2104 B.144 C.10 1.2105 B.145 C.10 1.2106 B.146 C.10 1.2107 B.147 C.10 1.2108 B.148 C.10 1.2109 B.149 C.10 1.2110 B.150 C.10 1.2111 B.151 C.10 1.2112 B.152 C.10 1.2113 B.153 C.10 1.2114 B.154 C.10 1.2115 B.155 C.10 1.2116 B.156 C.10 1.2117 B.157 C.10 1.2118 B.158 C.10 1.2119 B.159 C.10 1.2120 B.160 C.10 1.2121 B.161 C.10 1.2122 B.162 C.10 1.2123 B.163 C.10 1.2124 B.164 C.10 1.2125 B.165 C.10 1.2126 B.166 C.10 1.2127 B.167 C.10 1.2128 B.168 C.10 1.2129 B.169 C.10 1.2130 B.170 C.10 1.2131 B.171 C.10 1.2132 B.172 C.10 1.2133 B.173 C.10 1.2134 B.174 C.10 1.2135 B.175 C.10 1.2136 B.176 C.10 1.2137 B.177 C.10 1.2138 B.178 C.10 1.2139 B.179 C.10 1.2140 B.180 C.10 1.2141 B.181 C.10 1.2142 B.182 C.10 1.2143 B.183 C.10 1.2144 B.184 C.10 1.2145 B.185 C.10 1.2146 B.186 C.10 1.2147 B.187 C.10 1.2148 B.188 C.10 1.2149 B.189 C.10 1.2150 B.190 C.10 1.2151 B.191 C.10 1.2152 B.192 C.10 1.2153 B.193 C.10 1.2154 B.194 C.10 1.2155 B.195 C.10 1.2156 B.196 C.10 1.2157 B.1 C.11 1.2158 B.2 C.11 1.2159 B.3 C.11 1.2160 B.4 C.11 1.2161 B.5 C.11 1.2162 B.6 C.11 1.2163 B.7 C.11 1.2164 B.8 C.11 1.2165 B.9 C.11 1.2166 B.10 C.11 1.2167 B.11 C.11 1.2168 B.12 C.11 1.2169 B.13 C.11 1.2170 B.14 C.11 1.2171 B.15 C.11 1.2172 B.16 C.11 1.2173 B.17 C.11 1.2174 B.18 C.11 1.2175 B.19 C.11 1.2176 B.20 C.11 1.2177 B.21 C.11 1.2178 B.22 C.11 1.2179 B.23 C.11 1.2180 B.24 C.11 1.2181 B.25 C.11 1.2182 B.26 C.11 1.2183 B.27 C.11 1.2184 B.28 C.11 1.2185 B.29 C.11 1.2186 B.30 C.11 1.2187 B.31 C.11 1.2188 B.32 C.11 1.2189 B.33 C.11 1.2190 B.34 C.11 1.2191 B.35 C.11 1.2192 B.36 C.11 1.2193 B.37 C.11 1.2194 B.38 C.11 1.2195 B.39 C.11 1.2196 B.40 C.11 1.2197 B.41 C.11 1.2198 B.42 C.11 1.2199 B.43 C.11 1.2200 B.44 C.11 1.2201 B.45 C.11 1.2202 B.46 C.11 1.2203 B.47 C.11 1.2204 B.48 C.11 1.2205 B.49 C.11 1.2206 B.50 C.11 1.2207 B.51 C.11 1.2208 B.52 C.11 1.2209 B.53 C.11 1.2210 B.54 C.11 1.2211 B.55 C.11 1.2212 B.56 C.11 1.2213 B.57 C.11 1.2214 B.58. C.11 1.2215 B.59 C.11 1.2216 B.60 C.11 1.2217 B.61 C.11 1.2218 B.62 C.11 1.2219 B.63 C.11 1.2220 B.64 C.11 1.2221 B.65 C.11 1.2222 B.66 C.11 1.2223 B.67 C.11 1.2224 B.68 C.11 1.2225 B.69 C.11 1.2226 B.70 C.11 1.2227 B.71 C.11 1.2228 B.72 C.11 1.2229 B.73 C.11 1.2230 B.74 C.11 1.2231 B.75 C.11 1.2232 B.76 C.11 1.2233 B.77 C.11 1.2234 B.78 C.11 1.2235 B.79 C.11 1.2236 B.80 C.11 1.2237 B.81 C.11 1.2238 B.82 C.11 1.2239 B.83 C.11 1.2240 B.84 C.11 1.2241 B.85 C.11 1.2242 B.86 C.11 1.2243 B.87 C.11 1.2244 B.88 C.11 1.2245 B.89 C.11 1.2246 B.90 C.11 1.2247 B.91 C.11 1.2248 B.92 C.11 1.2249 B.93 C.11 1.2250 B.94 C.11 1.2251 B.95 C.11 1.2252 B.96 C.11 1.2253 B.97 C.11 1.2254 B.98 C.11 1.2255 B.99 C.11 1.2256 B.100 C.11 1.2257 B.101 C.11 1.2258 B.102 C.11 1.2259 B.103 C.11 1.2260 B.104 C.11 1.2261 B.105 C.11 1.2262 B.106 C.11 1.2263 B.107 C.11 1.2264 B.108 C.11 1.2265 B.109 C.11 1.2266 B.110 C.11 1.2267 B.111 C.11 1.2268 B.112 C.11 1.2269 B.113 C.11 1.2270 B.114 C.11 1.2271 B.115 C.11 1.2272 B.116 C.11 1.2273 B.117 C.11 1.2274 B.118 C.11 1.2275 B.119 C.11 1.2276 B.120 C.11 1.2277 B.121 C.11 1.2278 B.122 C.11 1.2279 B.123 C.11 1.2280 B.124 C.11 1.2281 B.125 C.11 1.2282 B.126 C.11 1.2283 B.127 C.11 1.2284 B.128 C.11 1.2285 B.129 C.11 1.2286 B.130 C.11 1.2287 B.131 C.11 1.2288 B.132 C.11 1.2289 B.133 C.11 1.2290 B.134 C.11 1.2291 B.135 C.11 1.2292 B.136 C.11 1.2293 B.137 C.11 1.2294 B.138 C.11 1.2295 B.139 C.11 1.2296 B.140 C.11 1.2297 B.141 C.11 1.2298 B.142 C.11 1.2299 B.143 C.11 1.2300 B.144 C.11 1.2301 B.145 C.11 1.2302 B.146 C.11 1.2303 B.147 C.11 1.2304 B.148 C.11 1.2305 B.149 C.11 1.2306 B.150 C.11 1.2307 B.151 C.11 1.2308 B.152 C.11 1.2309 B.153 C.11 1.2310 B.154 C.11 1.2311 B.155 C.11 1.2312 B.156 C.11 1.2313 B.157 C.11 1.2314 B.158 C.11 1.2315 B.159 C.11 1.2316 B.160 C.11 1.2317 B.161 C.11 1.2318 B.162 C.11 1.2319 B.163 C.11 1.2320 B.164 C.11 1.2321 B.165 C.11 1.2322 B.166 C.11 1.2323 B.167 C.11 1.2324 B.168 C.11 1.2325 B.169 C.11 1.2326 B.170 C.11 1.2327 B.171 C.11 1.2328 B.172 C.11 1.2329 B.173 C.11 1.2330 B.174 C.11 1.2331 B.175 C.11 1.2332 B.176 C.11 1.2333 B.177 C.11 1.2334 B.178 C.11 1.2335 B.179 C.11 1.2336 B.180 C.11 1.2337 B.181 C.11 1.2338 B.182 C.11 1.2339 B.183 C.11 1.2340 B.184 C.11 1.2341 B.185 C.11 1.2342 B.186 C.11 1.2343 B.187 C.11 1.2344 B.188 C.11 1.2345 B.189 C.11 1.2346 B.190 C.11 1.2347 B.191 C.11 1.2348 B.192 C.11 1.2349 B.193 C.11 1.2350 B.194 C.11 1.2351 B.195 C.11 1.2352 B.196 C.11 1.2353 B.1 C.12 1.2354 B.2 C.12 1.2355 B.3 C.12 1.2356 B.4 C.12 1.2357 B.5 C.12 1.2358 B.6 C.12 1.2359 B.7 C.12 1.2360 B.8 C.12 1.2361 B.9 C.12 1.2362 B.10 C.12 1.2363 B.11 C.12 1.2364 B.12 C.12 1.2365 B.13 C.12 1.2366 B.14 C.12 1.2367 B.15 C.12 1.2368 B.16 C.12 1.2369 B.17 C.12 1.2370 B.18 C.12 1.2371 B.19 C.12 1.2372 B.20 C.12 1.2373 B.21 C.12 1.2374 B.22 C.12 1.2375 B.23 C.12 1.2376 B.24 C.12 1.2377 B.25 C.12 1.2378 B.26 C.12 1.2379 B.27 C.12 1.2380 B.28 C.12 1.2381 B.29 C.12 1.2382 B.30 C.12 1.2383 B.31 C.12 1.2384 B.32 C.12 1.2385 B.33 C.12 1.2386 B.34 C.12 1.2387 B.35 C.12 1.2388 B.36 C.12 1.2389 B.37 C.12 1.2390 B.38 C.12 1.2391 B.39 C.12 1.2392 B.40 C.12 1.2393 B.41 C.12 1.2394 B.42 C.12 1.2395 B.43 C.12 1.2396 B.44 C.12 1.2397 B.45 C.12 1.2398 B.46 C.12 1.2399 B.47 C.12 1.2400 B.48 C.12 1.2401 B.49 C.12 1.2402 B.50 C.12 1.2403 B.51 C.12 1.2404 B.52 C.12 1.2405 B.53 C.12 1.2406 B.54 C.12 1.2407 B.55 C.12 1.2408 B.56 C.12 1.2409 B.57 C.12 1.2410 B.58. C.12 1.2411 B.59 C.12 1.2412 B.60 C.12 1.2413 B.61 C.12 1.2414 B.62 C.12 1.2415 B.63 C.12 1.2416 B.64 C.12 1.2417 B.65 C.12 1.2418 B.66 C.12 1.2419 B.67 C.12 1.2420 B.68 C.12 1.2421 B.69 C.12 1.2422 B.70 C.12 1.2423 B.71 C.12 1.2424 B.72 C.12 1.2425 B.73 C.12 1.2426 B.74 C.12 1.2427 B.75 C.12 1.2428 B.76 C.12 1.2429 B.77 C.12 1.2430 B.78 C.12 1.2431 B.79 C.12 1.2432 B.80 C.12 1.2433 B.81 C.12 1.2434 B.82 C.12 1.2435 B.83 C.12 1.2436 B.84 C.12 1.2437 B.85 C.12 1.2438 B.86 C.12 1.2439 B.87 C.12 1.2440 B.88 C.12 1.2441 B.89 C.12 1.2442 B.90 C.12 1.2443 B.91 C.12 1.2444 B.92 C.12 1.2445 B.93 C.12 1.2446 B.94 C.12 1.2447 B.95 C.12 1.2448 B.96 C.12 1.2449 B.97 C.12 1.2450 B.98 C.12 1.2451 B.99 C.12 1.2452 B.100 C.12 1.2453 B.101 C.12 1.2454 B.102 C.12 1.2455 B.103 C.12 1.2456 B.104 C.12 1.2457 B.105 C.12 1.2458 B.106 C.12 1.2459 B.107 C.12 1.2460 B.108 C.12 1.2461 B.109 C.12 1.2462 B.110 C.12 1.2463 B.111 C.12 1.2464 B.112 C.12 1.2465 B.113 C.12 1.2466 B.114 C.12 1.2467 B.115 C.12 1.2468 B.116 C.12 1.2469 B.117 C.12 1.2470 B.118 C.12 1.2471 B.119 C.12 1.2472 B.120 C.12 1.2473 B.121 C.12 1.2474 B.122 C.12 1.2475 B.123 C.12 1.2476 B.124 C.12 1.2477 B.125 C.12 1.2478 B.126 C.12 1.2479 B.127 C.12 1.2480 B.128 C.12 1.2481 B.129 C.12 1.2482 B.130 C.12 1.2483 B.131 C.12 1.2484 B.132 C.12 1.2485 B.133 C.12 1.2486 B.134 C.12 1.2487 B.135 C.12 1.2488 B.136 C.12 1.2489 B.137 C.12 1.2490 B.138 C.12 1.2491 B.139 C.12 1.2492 B.140 C.12 1.2493 B.141 C.12 1.2494 B.142 C.12 1.2495 B.143 C.12 1.2496 B.144 C.12 1.2497 B.145 C.12 1.2498 B.146 C.12 1.2499 B.147 C.12 1.2500 B.148 C.12 1.2501 B.149 C.12 1.2502 B.150 C.12 1.2503 B.151 C.12 1.2504 B.152 C.12 1.2505 B.153 C.12 1.2506 B.154 C.12 1.2507 B.155 C.12 1.2508 B.156 C.12 1.2509 B.157 C.12 1.2510 B.158 C.12 1.2511 B.159 C.12 1.2512 B.160 C.12 1.2513 B.161 C.12 1.2514 B.162 C.12 1.2515 B.163 C.12 1.2516 B.164 C.12 1.2517 B.165 C.12 1.2518 B.166 C.12 1.2519 B.167 C.12 1.2520 B.168 C.12 1.2521 B.169 C.12 1.2522 B.170 C.12 1.2523 B.171 C.12 1.2524 B.172 C.12 1.2525 B.173 C.12 1.2526 B.174 C.12 1.2527 B.175 C.12 1.2528 B.176 C.12 1.2529 B.177 C.12 1.2530 B.178 C.12 1.2531 B.179 C.12 1.2532 B.180 C.12 1.2533 B.181 C.12 1.2534 B.182 C.12 1.2535 B.183 C.12 1.2536 B.184 C.12 1.2537 B.185 C.12 1.2538 B.186 C.12 1.2539 B.187 C.12 1.2540 B.188 C.12 1.2541 B.189 C.12 1.2542 B.190 C.12 1.2543 B.191 C.12 1.2544 B.192 C.12 1.2545 B.193 C.12 1.2546 B.194 C.12 1.2547 B.195 C.12 1.2548 B.196 C.12 1.2549 B.1 C.13 1.2550 B.2 C.13 1.2551 B.3 C.13 1.2552 B.4 C.13 1.2553 B.5 C.13 1.2554 B.6 C.13 1.2555 B.7 C.13 1.2556 B.8 C.13 1.2557 B.9 C.13 1.2558 B.10 C.13 1.2559 B.11 C.13 1.2560 B.12 C.13 1.2561 B.13 C.13 1.2562 B.14 C.13 1.2563 B.15 C.13 1.2564 B.16 C.13 1.2565 B.17 C.13 1.2566 B.18 C.13 1.2567 B.19 C.13 1.2568 B.20 C.13 1.2569 B.21 C.13 1.2570 B.22 C.13 1.2571 B.23 C.13 1.2572 B.24 C.13 1.2573 B.25 C.13 1.2574 B.26 C.13 1.2575 B.27 C.13 1.2576 B.28 C.13 1.2577 B.29 C.13 1.2578 B.30 C.13 1.2579 B.31 C.13 1.2580 B.32 C.13 1.2581 B.33 C.13 1.2582 B.34 C.13 1.2583 B.35 C.13 1.2584 B.36 C.13 1.2585 B.37 C.13 1.2586 B.38 C.13 1.2587 B.39 C.13 1.2588 B.40 C.13 1.2589 B.41 C.13 1.2590 B.42 C.13 1.2591 B.43 C.13 1.2592 B.44 C.13 1.2593 B.45 C.13 1.2594 B.46 C.13 1.2595 B.47 C.13 1.2596 B.48 C.13 1.2597 B.49 C.13 1.2598 B.50 C.13 1.2599 B.51 C.13 1.2600 B.52 C.13 1.2601 B.53 C.13 1.2602 B.54 C.13 1.2603 B.55 C.13 1.2604 B.56 C.13 1.2605 B.57 C.13 1.2606 B.58. C.13 1.2607 B.59 C.13 1.2608 B.60 C.13 1.2609 B.61 C.13 1.2610 B.62 C.13 1.2611 B.63 C.13 1.2612 B.64 C.13 1.2613 B.65 C.13 1.2614 B.66 C.13 1.2615 B.67 C.13 1.2616 B.68 C.13 1.2617 B.69 C.13 1.2618 B.70 C.13 1.2619 B.71 C.13 1.2620 B.72 C.13 1.2621 B.73 C.13 1.2622 B.74 C.13 1.2623 B.75 C.13 1.2624 B.76 C.13 1.2625 B.77 C.13 1.2626 B.78 C.13 1.2627 B.79 C.13 1.2628 B.80 C.13 1.2629 B.81 C.13 1.2630 B.82 C.13 1.2631 B.83 C.13 1.2632 B.84 C.13 1.2633 B.85 C.13 1.2634 B.86 C.13 1.2635 B.87 C.13 1.2636 B.88 C.13 1.2637 B.89 C.13 1.2638 B.90 C.13 1.2639 B.91 C.13 1.2640 B.92 C.13 1.2641 B.93 C.13 1.2642 B.94 C.13 1.2643 B.95 C.13 1.2644 B.96 C.13 1.2645 B.97 C.13 1.2646 B.98 C.13 1.2647 B.99 C.13 1.2648 B.100 C.13 1.2649 B.101 C.13 1.2650 B.102 C.13 1.2651 B.103 C.13 1.2652 B.104 C.13 1.2653 B.105 C.13 1.2654 B.106 C.13 1.2655 B.107 C.13 1.2656 B.108 C.13 1.2657 B.109 C.13 1.2658 B.110 C.13 1.2659 B.111 C.13 1.2660 B.112 C.13 1.2661 B.113 C.13 1.2662 B.114 C.13 1.2663 B.115 C.13 1.2664 B.116 C.13 1.2665 B.117 C.13 1.2666 B.118 C.13 1.2667 B.119 C.13 1.2668 B.120 C.13 1.2669 B.121 C.13 1.2670 B.122 C.13 1.2671 B.123 C.13 1.2672 B.124 C.13 1.2673 B.125 C.13 1.2674 B.126 C.13 1.2675 B.127 C.13 1.2676 B.128 C.13 1.2677 B.129 C.13 1.2678 B.130 C.13 1.2679 B.131 C.13 1.2680 B.132 C.13 1.2681 B.133 C.13 1.2682 B.134 C.13 1.2683 B.135 C.13 1.2684 B.136 C.13 1.2685 B.137 C.13 1.2686 B.138 C.13 1.2687 B.139 C.13 1.2688 B.140 C.13 1.2689 B.141 C.13 1.2690 B.142 C.13 1.2691 B.143 C.13 1.2692 B.144 C.13 1.2693 B.145 C.13 1.2694 B.146 C.13 1.2695 B.147 C.13 1.2696 B.148 C.13 1.2697 B.149 C.13 1.2698 B.150 C.13 1.2699 B.151 C.13 1.2700 B.152 C.13 1.2701 B.153 C.13 1.2702 B.154 C.13 1.2703 B.155 C.13 1.2704 B.156 C.13 1.2705 B.157 C.13 1.2706 B.158 C.13 1.2707 B.159 C.13 1.2708 B.160 C.13 1.2709 B.161 C.13 1.2710 B.162 C.13 1.2711 B.163 C.13 1.2712 B.164 C.13 1.2713 B.165 C.13 1.2714 B.166 C.13 1.2715 B.167 C.13 1.2716 B.168 C.13 1.2717 B.169 C.13 1.2718 B.170 C.13 1.2719 B.171 C.13 1.2720 B.172 C.13 1.2721 B.173 C.13 1.2722 B.174 C.13 1.2723 B.175 C.13 1.2724 B.176 C.13 1.2725 B.177 C.13 1.2726 B.178 C.13 1.2727 B.179 C.13 1.2728 B.180 C.13 1.2729 B.181 C.13 1.2730 B.182 C.13 1.2731 B.183 C.13 1.2732 B.184 C.13 1.2733 B.185 C.13 1.2734 B.186 C.13 1.2735 B.187 C.13 1.2736 B.188 C.13 1.2737 B.189 C.13 1.2738 B.190 C.13 1.2739 B.191 C.13 1.2740 B.192 C.13 1.2741 B.193 C.13 1.2742 B.194 C.13 1.2743 B.195 C.13 1.2744 B.196 C.13 1.2745 B.1 C.14 1.2746 B.2 C.14 1.2747 B.3 C.14 1.2748 B.4 C.14 1.2749 B.5 C.14 1.2750 B.6 C.14 1.2751 B.7 C.14 1.2752 B.8 C.14 1.2753 B.9 C.14 1.2754 B.10 C.14 1.2755 B.11 C.14 1.2756 B.12 C.14 1.2757 B.13 C.14 1.2758 B.14 C.14 1.2759 B.15 C.14 1.2760 B.16 C.14 1.2761 B.17 C.14 1.2762 B.18 C.14 1.2763 B.19 C.14 1.2764 B.20 C.14 1.2765 B.21 C.14 1.2766 B.22 C.14 1.2767 B.23 C.14 1.2768 B.24 C.14 1.2769 B.25 C.14 1.2770 B.26 C.14 1.2771 B.27 C.14 1.2772 B.28 C.14 1.2773 B.29 C.14 1.2774 B.30 C.14 1.2775 B.31 C.14 1.2776 B.32 C.14 1.2777 B.33 C.14 1.2778 B.34 C.14 1.2779 B.35 C.14 1.2780 B.36 C.14 1.2781 B.37 C.14 1.2782 B.38 C.14 1.2783 B.39 C.14 1.2784 B.40 C.14 1.2785 B.41 C.14 1.2786 B.42 C.14 1.2787 B.43 C.14 1.2788 B.44 C.14 1.2789 B.45 C.14 1.2790 B.46 C.14 1.2791 B.47 C.14 1.2792 B.48 C.14 1.2793 B.49 C.14 1.2794 B.50 C.14 1.2795 B.51 C.14 1.2796 B.52 C.14 1.2797 B.53 C.14 1.2798 B.54 C.14 1.2799 B.55 C.14 1.2800 B.56 C.14 1.2801 B.57 C.14 1.2802 B.58. C.14 1.2803 B.59 C.14 1.2804 B.60 C.14 1.2805 B.61 C.14 1.2806 B.62 C.14 1.2807 B.63 C.14 1.2808 B.64 C.14 1.2809 B.65 C.14 1.2810 B.66 C.14 1.2811 B.67 C.14 1.2812 B.68 C.14 1.2813 B.69 C.14 1.2814 B.70 C.14 1.2815 B.71 C.14 1.2816 B.72 C.14 1.2817 B.73 C.14 1.2818 B.74 C.14 1.2819 B.75 C.14 1.2820 B.76 C.14 1.2821 B.77 C.14 1.2822 B.78 C.14 1.2823 B.79 C.14 1.2824 B.80 C.14 1.2825 B.81 C.14 1.2826 B.82 C.14 1.2827 B.83 C.14 1.2828 B.84 C.14 1.2829 B.85 C.14 1.2830 B.86 C.14 1.2831 B.87 C.14 1.2832 B.88 C.14 1.2833 B.89 C.14 1.2834 B.90 C.14 1.2835 B.91 C.14 1.2836 B.92 C.14 1.2837 B.93 C.14 1.2838 B.94 C.14 1.2839 B.95 C.14 1.2840 B.96 C.14 1.2841 B.97 C.14 1.2842 B.98 C.14 1.2843 B.99 C.14 1.2844 B.100 C.14 1.2845 B.101 C.14 1.2846 B.102 C.14 1.2847 B.103 C.14 1.2848 B.104 C.14 1.2849 B.105 C.14 1.2850 B.106 C.14 1.2851 B.107 C.14 1.2852 B.108 C.14 1.2853 B.109 C.14 1.2854 B.110 C.14 1.2855 B.111 C.14 1.2856 B.112 C.14 1.2857 B.113 C.14 1.2858 B.114 C.14 1.2859 B.115 C.14 1.2860 B.116 C.14 1.2861 B.117 C.14 1.2862 B.118 C.14 1.2863 B.119 C.14 1.2864 B.120 C.14 1.2865 B.121 C.14 1.2866 B.122 C.14 1.2867 B.123 C.14 1.2868 B.124 C.14 1.2869 B.125 C.14 1.2870 B.126 C.14 1.2871 B.127 C.14 1.2872 B.128 C.14 1.2873 B.129 C.14 1.2874 B.130 C.14 1.2875 B.131 C.14 1.2876 B.132 C.14 1.2877 B.133 C.14 1.2878 B.134 C.14 1.2879 B.135 C.14 1.2880 B.136 C.14 1.2881 B.137 C.14 1.2882 B.138 C.14 1.2883 B.139 C.14 1.2884 B.140 C.14 1.2885 B.141 C.14 1.2886 B.142 C.14 1.2887 B.143 C.14 1.2888 B.144 C.14 1.2889 B.145 C.14 1.2890 B.146 C.14 1.2891 B.147 C.14 1.2892 B.148 C.14 1.2893 B.149 C.14 1.2894 B.150 C.14 1.2895 B.151 C.14 1.2896 B.152 C.14 1.2897 B.153 C.14 1.2898 B.154 C.14 1.2899 B.155 C.14 1.2900 B.156 C.14 1.2901 B.157 C.14 1.2902 B.158 C.14 1.2903 B.159 C.14 1.2904 B.160 C.14 1.2905 B.161 C.14 1.2906 B.162 C.14 1.2907 B.163 C.14 1.2908 B.164 C.14 1.2909 B.165 C.14 1.2910 B.166 C.14 1.2911 B.167 C.14 1.2912 B.168 C.14 1.2913 B.169 C.14 1.2914 B.170 C.14 1.2915 B.171 C.14 1.2916 B.172 C.14 1.2917 B.173 C.14 1.2918 B.174 C.14 1.2919 B.175 C.14 1.2920 B.176 C.14 1.2921 B.177 C.14 1.2922 B.178 C.14 1.2923 B.179 C.14 1.2924 B.180 C.14 1.2925 B.181 C.14 1.2926 B.182 C.14 1.2927 B.183 C.14 1.2928 B.184 C.14 1.2929 B.185 C.14 1.2930 B.186 C.14 1.2931 B.187 C.14 1.2932 B.188 C.14 1.2933 B.189 C.14 1.2934 B.190 C.14 1.2935 B.191 C.14 1.2936 B.192 C.14 1.2937 B.193 C.14 1.2938 B.194 C.14 1.2939 B.195 C.14 1.2940 B.196 C.14 1.2941 B.1 C.15 1.2942 B.2 C.15 1.2943 B.3 C.15 1.2944 B.4 C.15 1.2945 B.5 C.15 1.2946 B.6 C.15 1.2947 B.7 C.15 1.2948 B.8 C.15 1.2949 B.9 C.15 1.2950 B.10 C.15 1.2951 B.11 C.15 1.2952 B.12 C.15 1.2953 B.13 C.15 1.2954 B.14 C.15 1.2955 B.15 C.15 1.2956 B.16 C.15 1.2957 B.17 C.15 1.2958 B.18 C.15 1.2959 B.19 C.15 1.2960 B.20 C.15 1.2961 B.21 C.15 1.2962 B.22 C.15 1.2963 B.23 C.15 1.2964 B.24 C.15 1.2965 B.25 C.15 1.2966 B.26 C.15 1.2967 B.27 C.15 1.2968 B.28 C.15 1.2969 B.29 C.15 1.2970 B.30 C.15 1.2971 B.31 C.15 1.2972 B.32 C.15 1.2973 B.33 C.15 1.2974 B.34 C.15 1.2975 B.35 C.15 1.2976 B.36 C.15 1.2977 B.37 C.15 1.2978 B.38 C.15 1.2979 B.39 C.15 1.2980 B.40 C.15 1.2981 B.41 C.15 1.2982 B.42 C.15 1.2983 B.43 C.15 1.2984 B.44 C.15 1.2985 B.45 C.15 1.2986 B.46 C.15 1.2987 B.47 C.15 1.2988 B.48 C.15 1.2989 B.49 C.15 1.2990 B.50 C.15 1.2991 B.51 C.15 1.2992 B.52 C.15 1.2993 B.53 C.15 1.2994 B.54 C.15 1.2995 B.55 C.15 1.2996 B.56 C.15 1.2997 B.57 C.15 1.2998 B.58. C.15 1.2999 B.59 C.15 1.3000 B.60 C.15 1.3001 B.61 C.15 1.3002 B.62 C.15 1.3003 B.63 C.15 1.3004 B.64 C.15 1.3005 B.65 C.15 1.3006 B.66 C.15 1.3007 B.67 C.15 1.3008 B.68 C.15 1.3009 B.69 C.15 1.3010 B.70 C.15 1.3011 B.71 C.15 1.3012 B.72 C.15 1.3013 B.73 C.15 1.3014 B.74 C.15 1.3015 B.75 C.15 1.3016 B.76 C.15 1.3017 B.77 C.15 1.3018 B.78 C.15 1.3019 B.79 C.15 1.3020 B.80 C.15 1.3021 B.81 C.15 1.3022 B.82 C.15 1.3023 B.83 C.15 1.3024 B.84 C.15 1.3025 B.85 C.15 1.3026 B.86 C.15 1.3027 B.87 C.15 1.3028 B.88 C.15 1.3029 B.89 C.15 1.3030 B.90 C.15 1.3031 B.91 C.15 1.3032 B.92 C.15 1.3033 B.93 C.15 1.3034 B.94 C.15 1.3035 B.95 C.15 1.3036 B.96 C.15 1.3037 B.97 C.15 1.3038 B.98 C.15 1.3039 B.99 C.15 1.3040 B.100 C.15 1.3041 B.101 C.15 1.3042 B.102 C.15 1.3043 B.103 C.15 1.3044 B.104 C.15 1.3045 B.105 C.15 1.3046 B.106 C.15 1.3047 B.107 C.15 1.3048 B.108 C.15 1.3049 B.109 C.15 1.3050 B.110 C.15 1.3051 B.111 C.15 1.3052 B.112 C.15 1.3053 B.113 C.15 1.3054 B.114 C.15 1.3055 B.115 C.15 1.3056 B.116 C.15 1.3057 B.117 C.15 1.3058 B.118 C.15 1.3059 B.119 C.15 1.3060 B.120 C.15 1.3061 B.121 C.15 1.3062 B.122 C.15 1.3063 B.123 C.15 1.3064 B.124 C.15 1.3065 B.125 C.15 1.3066 B.126 C.15 1.3067 B.127 C.15 1.3068 B.128 C.15 1.3069 B.129 C.15 1.3070 B.130 C.15 1.3071 B.131 C.15 1.3072 B.132 C.15 1.3073 B.133 C.15 1.3074 B.134 C.15 1.3075 B.135 C.15 1.3076 B.136 C.15 1.3077 B.137 C.15 1.3078 B.138 C.15 1.3079 B.139 C.15 1.3080 B.140 C.15 1.3081 B.141 C.15 1.3082 B.142 C.15 1.3083 B.143 C.15 1.3084 B.144 C.15 1.3085 B.145 C.15 1.3086 B.146 C.15 1.3087 B.147 C.15 1.3088 B.148 C.15 1.3089 B.149 C.15 1.3090 B.150 C.15 1.3091 B.151 C.15 1.3092 B.152 C.15 1.3093 B.153 C.15 1.3094 B.154 C.15 1.3095 B.155 C.15 1.3096 B.156 C.15 1.3097 B.157 C.15 1.3098 B.158 C.15 1.3099 B.159 C.15 1.3100 B.160 C.15 1.3101 B.161 C.15 1.3102 B.162 C.15 1.3103 B.163 C.15 1.3104 B.164 C.15 1.3105 B.165 C.15 1.3106 B.166 C.15 1.3107 B.167 C.15 1.3108 B.168 C.15 1.3109 B.169 C.15 1.3110 B.170 C.15 1.3111 B.171 C.15 1.3112 B.172 C.15 1.3113 B.173 C.15 1.3114 B.174 C.15 1.3115 B.175 C.15 1.3116 B.176 C.15 1.3117 B.177 C.15 1.3118 B.178 C.15 1.3119 B.179 C.15 1.3120 B.180 C.15 1.3121 B.181 C.15 1.3122 B.182 C.15 1.3123 B.183 C.15 1.3124 B.184 C.15 1.3125 B.185 C.15 1.3126 B.186 C.15 1.3127 B.187 C.15 1.3128 B.188 C.15 1.3129 B.189 C.15 1.3130 B.190 C.15 1.3131 B.191 C.15 1.3132 B.192 C.15 1.3133 B.193 C.15 1.3134 B.194 C.15 1.3135 B.195 C.15 1.3136 B.196 C.15 1.3137 B.1 C.16 1.3138 B.2 C.16 1.3139 B.3 C.16 1.3140 B.4 C.16 1.3141 B.5 C.16 1.3142 B.6 C.16 1.3143 B.7 C.16 1.3144 B.8 C.16 1.3145 B.9 C.16 1.3146 B.10 C.16 1.3147 B.11 C.16 1.3148 B.12 C.16 1.3149 B.13 C.16 1.3150 B.14 C.16 1.3151 B.15 C.16 1.3152 B.16 C.16 1.3153 B.17 C.16 1.3154 B.18 C.16 1.3155 B.19 C.16 1.3156 B.20 C.16 1.3157 B.21 C.16 1.3158 B.22 C.16 1.3159 B.23 C.16 1.3160 B.24 C.16 1.3161 B.25 C.16 1.3162 B.26 C.16 1.3163 B.27 C.16 1.3164 B.28 C.16 1.3165 B.29 C.16 1.3166 B.30 C.16 1.3167 B.31 C.16 1.3168 B.32 C.16 1.3169 B.33 C.16 1.3170 B.34 C.16 1.3171 B.35 C.16 1.3172 B.36 C.16 1.3173 B.37 C.16 1.3174 B.38 C.16 1.3175 B.39 C.16 1.3176 B.40 C.16 1.3177 B.41 C.16 1.3178 B.42 C.16 1.3179 B.43 C.16 1.3180 B.44 C.16 1.3181 B.45 C.16 1.3182 B.46 C.16 1.3183 B.47 C.16 1.3184 B.48 C.16 1.3185 B.49 C.16 1.3186 B.50 C.16 1.3187 B.51 C.16 1.3188 B.52 C.16 1.3189 B.53 C.16 1.3190 B.54 C.16 1.3191 B.55 C.16 1.3192 B.56 C.16 1.3193 B.57 C.16 1.3194 B.58. C.16 1.3195 B.59 C.16 1.3196 B.60 C.16 1.3197 B.61 C.16 1.3198 B.62 C.16 1.3199 B.63 C.16 1.3200 B.64 C.16 1.3201 B.65 C.16 1.3202 B.66 C.16 1.3203 B.67 C.16 1.3204 B.68 C.16 1.3205 B.69 C.16 1.3206 B.70 C.16 1.3207 B.71 C.16 1.3208 B.72 C.16 1.3209 B.73 C.16 1.3210 B.74 C.16 1.3211 B.75 C.16 1.3212 B.76 C.16 1.3213 B.77 C.16 1.3214 B.78 C.16 1.3215 B.79 C.16 1.3216 B.80 C.16 1.3217 B.81 C.16 1.3218 B.82 C.16 1.3219 B.83 C.16 1.3220 B.84 C.16 1.3221 B.85 C.16 1.3222 B.86 C.16 1.3223 B.87 C.16 1.3224 B.88 C.16 1.3225 B.89 C.16 1.3226 B.90 C.16 1.3227 B.91 C.16 1.3228 B.92 C.16 1.3229 B.93 C.16 1.3230 B.94 C.16 1.3231 B.95 C.16 1.3232 B.96 C.16 1.3233 B.97 C.16 1.3234 B.98 C.16 1.3235 B.99 C.16 1.3236 B.100 C.16 1.3237 B.101 C.16 1.3238 B.102 C.16 1.3239 B.103 C.16 1.3240 B.104 C.16 1.3241 B.105 C.16 1.3242 B.106 C.16 1.3243 B.107 C.16 1.3244 B.108 C.16 1.3245 B.109 C.16 1.3246 B.110 C.16 1.3247 B.111 C.16 1.3248 B.112 C.16 1.3249 B.113 C.16 1.3250 B.114 C.16 1.3251 B.115 C.16 1.3252 B.116 C.16 1.3253 B.117 C.16 1.3254 B.118 C.16 1.3255 B.119 C.16 1.3256 B.120 C.16 1.3257 B.121 C.16 1.3258 B.122 C.16 1.3259 B.123 C.16 1.3260 B.124 C.16 1.3261 B.125 C.16 1.3262 B.126 C.16 1.3263 B.127 C.16 1.3264 B.128 C.16 1.3265 B.129 C.16 1.3266 B.130 C.16 1.3267 B.131 C.16 1.3268 B.132 C.16 1.3269 B.133 C.16 1.3270 B.134 C.16 1.3271 B.135 C.16 1.3272 B.136 C.16 1.3273 B.137 C.16 1.3274 B.138 C.16 1.3275 B.139 C.16 1.3276 B.140 C.16 1.3277 B.141 C.16 1.3278 B.142 C.16 1.3279 B.143 C.16 1.3280 B.144 C.16 1.3281 B.145 C.16 1.3282 B.146 C.16 1.3283 B.147 C.16 1.3284 B.148 C.16 1.3285 B.149 C.16 1.3286 B.150 C.16 1.3287 B.151 C.16 1.3288 B.152 C.16 1.3289 B.153 C.16 1.3290 B.154 C.16 1.3291 B.155 C.16 1.3292 B.156 C.16 1.3293 B.157 C.16 1.3294 B.158 C.16 1.3295 B.159 C.16 1.3296 B.160 C.16 1.3297 B.161 C.16 1.3298 B.162 C.16 1.3299 B.163 C.16 1.3300 B.164 C.16 1.3301 B.165 C.16 1.3302 B.166 C.16 1.3303 B.167 C.16 1.3304 B.168 C.16 1.3305 B.169 C.16 1.3306 B.170 C.16 1.3307 B.171 C.16 1.3308 B.172 C.16 1.3309 B.173 C.16 1.3310 B.174 C.16 1.3311 B.175 C.16 1.3312 B.176 C.16 1.3313 B.177 C.16 1.3314 B.178 C.16 1.3315 B.179 C.16 1.3316 B.180 C.16 1.3317 B.181 C.16 1.3318 B.182 C.16 1.3319 B.183 C.16 1.3320 B.184 C.16 1.3321 B.185 C.16 1.3322 B.186 C.16 1.3323 B.187 C.16 1.3324 B.188 C.16 1.3325 B.189 C.16 1.3326 B.190 C.16 1.3327 B.191 C.16 1.3328 B.192 C.16 1.3329 B.193 C.16 1.3330 B.194 C.16 1.3331 B.195 C.16 1.3332 B.196 C.16 1.3333 B.1 C.17 1.3334 B.2 C.17 1.3335 B.3 C.17 1.3336 B.4 C.17 1.3337 B.5 C.17 1.3338 B.6 C.17 1.3339 B.7 C.17 1.3340 B.8 C.17 1.3341 B.9 C.17 1.3342 B.10 C.17 1.3343 B.11 C.17 1.3344 B.12 C.17 1.3345 B.13 C.17 1.3346 B.14 C.17 1.3347 B.15 C.17 1.3348 B.16 C.17 1.3349 B.17 C.17 1.3350 B.18 C.17 1.3351 B.19 C.17 1.3352 B.20 C.17 1.3353 B.21 C.17 1.3354 B.22 C.17 1.3355 B.23 C.17 1.3356 B.24 C.17 1.3357 B.25 C.17 1.3358 B.26 C.17 1.3359 B.27 C.17 1.3360 B.28 C.17 1.3361 B.29 C.17 1.3362 B.30 C.17 1.3363 B.31 C.17 1.3364 B.32 C.17 1.3365 B.33 C.17 1.3366 B.34 C.17 1.3367 B.35 C.17 1.3368 B.36 C.17 1.3369 B.37 C.17 1.3370 B.38 C.17 1.3371 B.39 C.17 1.3372 B.40 C.17 1.3373 B.41 C.17 1.3374 B.42 C.17 1.3375 B.43 C.17 1.3376 B.44 C.17 1.3377 B.45 C.17 1.3378 B.46 C.17 1.3379 B.47 C.17 1.3380 B.48 C.17 1.3381 B.49 C.17 1.3382 B.50 C.17 1.3383 B.51 C.17 1.3384 B.52 C.17 1.3385 B.53 C.17 1.3386 B.54 C.17 1.3387 B.55 C.17 1.3388 B.56 C.17 1.3389 B.57 C.17 1.3390 B.58. C.17 1.3391 B.59 C.17 1.3392 B.60 C.17 1.3393 B.61 C.17 1.3394 B.62 C.17 1.3395 B.63 C.17 1.3396 B.64 C.17 1.3397 B.65 C.17 1.3398 B.66 C.17 1.3399 B.67 C.17 1.3400 B.68 C.17 1.3401 B.69 C.17 1.3402 B.70 C.17 1.3403 B.71 C.17 1.3404 B.72 C.17 1.3405 B.73 C.17 1.3406 B.74 C.17 1.3407 B.75 C.17 1.3408 B.76 C.17 1.3409 B.77 C.17 1.3410 B.78 C.17 1.3411 B.79 C.17 1.3412 B.80 C.17 1.3413 B.81 C.17 1.3414 B.82 C.17 1.3415 B.83 C.17 1.3416 B.84 C.17 1.3417 B.85 C.17 1.3418 B.86 C.17 1.3419 B.87 C.17 1.3420 B.88 C.17 1.3421 B.89 C.17 1.3422 B.90 C.17 1.3423 B.91 C.17 1.3424 B.92 C.17 1.3425 B.93 C.17 1.3426 B.94 C.17 1.3427 B.95 C.17 1.3428 B.96 C.17 1.3429 B.97 C.17 1.3430 B.98 C.17 1.3431 B.99 C.17 1.3432 B.100 C.17 1.3433 B.101 C.17 1.3434 B.102 C.17 1.3435 B.103 C.17 1.3436 B.104 C.17 1.3437 B.105 C.17 1.3438 B.106 C.17 1.3439 B.107 C.17 1.3440 B.108 C.17 1.3441 B.109 C.17 1.3442 B.110 C.17 1.3443 B.111 C.17 1.3444 B.112 C.17 1.3445 B.113 C.17 1.3446 B.114 C.17 1.3447 B.115 C.17 1.3448 B.116 C.17 1.3449 B.117 C.17 1.3450 B.118 C.17 1.3451 B.119 C.17 1.3452 B.120 C.17 1.3453 B.121 C.17 1.3454 B.122 C.17 1.3455 B.123 C.17 1.3456 B.124 C.17 1.3457 B.125 C.17 1.3458 B.126 C.17 1.3459 B.127 C.17 1.3460 B.128 C.17 1.3461 B.129 C.17 1.3462 B.130 C.17 1.3463 B.131 C.17 1.3464 B.132 C.17 1.3465 B.133 C.17 1.3466 B.134 C.17 1.3467 B.135 C.17 1.3468 B.136 C.17 1.3469 B.137 C.17 1.3470 B.138 C.17 1.3471 B.139 C.17 1.3472 B.140 C.17 1.3473 B.141 C.17 1.3474 B.142 C.17 1.3475 B.143 C.17 1.3476 B.144 C.17 1.3477 B.145 C.17 1.3478 B.146 C.17 1.3479 B.147 C.17 1.3480 B.148 C.17 1.3481 B.149 C.17 1.3482 B.150 C.17 1.3483 B.151 C.17 1.3484 B.152 C.17 1.3485 B.153 C.17 1.3486 B.154 C.17 1.3487 B.155 C.17 1.3488 B.156 C.17 1.3489 B.157 C.17 1.3490 B.158 C.17 1.3491 B.159 C.17 1.3492 B.160 C.17 1.3493 B.161 C.17 1.3494 B.162 C.17 1.3495 B.163 C.17 1.3496 B.164 C.17 1.3497 B.165 C.17 1.3498 B.166 C.17 1.3499 B.167 C.17 1.3500 B.168 C.17 1.3501 B.169 C.17 1.3502 B.170 C.17 1.3503 B.171 C.17 1.3504 B.172 C.17 1.3505 B.173 C.17 1.3506 B.174 C.17 1.3507 B.175 C.17 1.3508 B.176 C.17 1.3509 B.177 C.17 1.3510 B.178 C.17 1.3511 B.179 C.17 1.3512 B.180 C.17 1.3513 B.181 C.17 1.3514 B.182 C.17 1.3515 B.183 C.17 1.3516 B.184 C.17 1.3517 B.185 C.17 1.3518 B.186 C.17 1.3519 B.187 C.17 1.3520 B.188 C.17 1.3521 B.189 C.17 1.3522 B.190 C.17 1.3523 B.191 C.17 1.3524 B.192 C.17 1.3525 B.193 C.17 1.3526 B.194 C.17 1.3527 B.195 C.17 1.3528 B.196 C.17 1.3529 — C.1 1.3530 — C.2 1.3531 — C.3 1.3532 — C.4 1.3533 — C.5 1.3534 — C.6 1.3535 — C.7 1.3536 — C.8 1.3537 — C.9 1.3538 — C.10 1.3539 — C.11 1.3540 — C.12 1.3541 — C.13 1.3542 — C.14 1.3543 — C.15 1.3544 — C.16 1.3545 — C.17

The specific number for each single composition is deductible as follows: Composition 1.200 for example comprises compounds of formula (I) cyhalofop-butyl (B.4) and benoxacor (C.1).

Composition 2.200 for example comprises the compounds of formula (I) (see the definition for compositions 2.1 to 2.3545 below), cyhalofop-butyl (B.4) and benoxacor (C.1).

Composition 7.200 for example comprises compounds of formula (I) imazapyr (B.35), cyhalofop-butyl (B.4) and benoxacor (C.1.

Also especially preferred are compositions 2.1. to 2.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they comprise as the active compound A the compounds of formula (Ia).

Also especially preferred are compositions 3.1. to 3.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.2 clodinafop-propargyl as further herbicide B.

Also especially preferred are compositions 4.1. to 4.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.8 pinoxaden as further herbicide B.

Also especially preferred are compositions 5.1. to 5.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.30 imazamox as further herbicide B.

Also especially preferred are compositions 6.1. to 6.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.32 imazapic as further herbicide B.

Also especially preferred are compositions 7.1. to 7.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.35 imazapyr as further herbicide B.

Also especially preferred are compositions 8.1. to 8.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.38 imazaquin as further herbicide B.

Also especially preferred are compositions 9.1. to 9.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.40 imazethapyr as further herbicide B.

Also especially preferred are compositions 10.1. to 10.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.51 nicosulfuron as further herbicide B.

Also especially preferred are compositions 11.1. to 11.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.55 pyribenzoxim as further herbicide B.

Also especially preferred are compositions 12.1. to 12.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.56 pyriftalid as further herbicide B.

Also especially preferred are compositions 13.1. to 13.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.64 tritosulfuron as further herbicide B.

Also especially preferred are compositions 14.1. to 14.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.66 ametryne as further herbicide B.

Also especially preferred are compositions 15.1. to 15.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.67 atrazine as further herbicide B.

Also especially preferred are compositions 16.1. to 16.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.68 bentazon as further herbicide B.

Also especially preferred are compositions 17.1. to 17.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.69 bromoxynil as further herbicide B.

Also especially preferred are compositions 18.1. to 18.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.73 diuron as further herbicide B.

Also especially preferred are compositions 19.1. to 19.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.76 isoproturon as further herbicide B.

Also especially preferred are compositions 20.1. to 20.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.81 simazin as further herbicide B.

Also especially preferred are compositions 21.1. to 21.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.82 terbuthylazin as further herbicide B.

Also especially preferred are compositions 22.1. to 22.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.85 acifluorfen as further herbicide B.

Also especially preferred are compositions 23.1. to 23.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.88 flumioxazin as further herbicide B.

Also especially preferred are compositions 24.1. to 24.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.89 fomesafen as further herbicide B.

Also especially preferred are compositions 25.1. to 25.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.94 saflufenacil as further herbicide B.

Also especially preferred are compositions 26.1. to 26.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.95 sulfentrazone as further herbicide B.

Also especially preferred are compositions 27.1. to 27.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.98 benzbicyclone as further herbicide B.

Also especially preferred are compositions 28.1. to 28.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.100 clomazone as further herbicide B.

Also especially preferred are compositions 29.1. to 29.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.103 isoxaflutole as further herbicide B.

Also especially preferred are compositions 30.1. to 30.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.103 isoxaflutole and B.67 atrazine as further herbicides B.

Also especially preferred are compositions 31.1. to 31.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.103 isoxaflutole and B.76 isoproturon as further herbicides B.

Also especially preferred are compositions 32.1. to 32.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.103 isoxaflutole and B.82 terbutylazin as further herbicides B.

Also especially preferred are compositions 33.1. to 33.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.104 mesotrione as further herbicide B.

Also especially preferred are compositions 34.1. to 34.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.104 mesotrione and B.67 atrazine as further herbicides B.

Also especially preferred are compositions 35.1. to 35.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.104 mesotrione and B.76 isoproturon as further herbicides B.

Also especially preferred are compositions 36.1. to 36.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.104 mesotrione and B.82 terbutylazin as further herbicides B.

Also especially preferred are compositions 37.1. to 37.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.106 picolinafen as further herbicide B.

Also especially preferred are compositions 38.1. to 38.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.107 sulcotrione as further herbicide B.

Also especially preferred are compositions 39.1. to 39.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B. 107 sulcotrione and B.67 atrazine as further herbicides B.

Also especially preferred are compositions 40.1. to 40.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B. 107 sulcotrione and B.76 isoproturon as further herbicides B.

Also especially preferred are compositions 41.1. to 41.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B. 107 sulcotrione and B.82 terbutylazin as further herbicides B.

Also especially preferred are compositions 42.1. to 42.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.109 tembotrione as further herbicide B.

Also especially preferred are compositions 43.1. to 43.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.111 topramezone as further herbicide B.

Also especially preferred are compositions 44.1. to 44.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.111 topramezone and B.67 atrazine as further herbicides B.

Also especially preferred are compositions 45.1. to 45.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.111 topramezone and B.76 isoproturon as further herbicides B.

Also especially preferred are compositions 46.1. to 46.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.111 topramezone and B.82 terbutylazin as further herbicides B.

Also especially preferred are compositions 47.1. to 47.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.116 glyphosate as further herbicide B.

Also especially preferred are compositions 48.1. to 48.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.116 glyphosate and B.67 atrazine as further herbicides B.

Also especially preferred are compositions 49.1. to 49.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.116 glyphosate and B.94 saflufenacil as further herbicides B.

Also especially preferred are compositions 50.1. to 50.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.116 glyphosate and B.103 isoxaflutole as further herbicides B.

Also especially preferred are compositions 51.1. to 51.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.116 glyphosate and B.128 acetochlor as further herbicides B.

Also especially preferred are compositions 52.1. to 52.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.116 glyphosate and B.104 mesotrione as further herbicides B.

Also especially preferred are compositions 53.1. to 53.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.116 glyphosate and B.107 sulcotrione as further herbicides B.

Also especially preferred are compositions 54.1. to 54.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.116 glyphosate and B.111 topramezone as further herbicides B.

Also especially preferred are compositions 55.1. to 55.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.122 glufosinate as further herbicide B.

Also especially preferred are compositions 56.1. to 56.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.126 pendimethalin as further herbicide B.

Also especially preferred are compositions 57.1. to 57.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.128 acetochlor as further herbicide B.

Also especially preferred are compositions 58.1. to 58.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.131 dimethenamid-P as further herbicide B.

Also especially preferred are compositions 59.1. to 59.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.132 fentrazamide as further herbicide B.

Also especially preferred are compositions 60.1. to 60.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.133 flufenacet as further herbicide B.

Also especially preferred are compositions 61.1. to 61.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.135 metazachlor as further herbicide B.

Also especially preferred are compositions 62.1. to 62.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.137 S-metolachlor as further herbicide B.

Also especially preferred are compositions 63.1. to 63.3545 which differ from the corresponding compositions 11.1 to 1.3545 only in that they additionally comprise B.138 pretilachlor as further herbicide B.

Also especially preferred are compositions 64.1. to 64.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.140 indaziflam as further herbicide B.

Also especially preferred are compositions 65.1. to 65.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.145 2,4-D as further herbicide B.

Also especially preferred are compositions 66.1. to 66.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.153 clopyralid as further herbicide B.

Also especially preferred are compositions 67.1. to 67.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.156 dicamba as further herbicide B.

Also especially preferred are compositions 68.1. to 68.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.171 MCPA as further herbicide B.

Also especially preferred are compositions 69.1. to 69.3545 which differ from the corresponding compositions 1.1 to 1.3545 only in that they additionally comprise B.174 quinclorac as further herbicide B.

The invention also relates to agrochemical compositions comprising an auxiliary and at least one diaminotriazine compound of formula (I) or a composition according to the invention.

An agrochemical diaminotriazine compound of formula (I) or a composition comprises a pesticidally effective amount of at least one composition according to the invention. The term “effective amount” denotes an amount of the active ingredients, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic conditions and the specific composition according to the invention used.

The diaminotriazine compounds of formula (I) (compounds A) and optionally B and/or C, their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6^(th) Ed. May 2008, CropLife International.

The agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl-naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidones, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for agrochemical composition types and their preparation are:

i) Water-Soluble Concentrates (SL, LS)

10-60 wt % of a compound of formula (I) or composition according to the invention and 5-15 wt % wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt %. The active substance dissolves upon dilution with water.

ii) Dispersible Concentrates (DC)

5-25 wt % of a diamonitriazine compound of formula (I) or composition according to the invention and 1-10 wt % dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt %. Dilution with water gives a dispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt % of a diamonitriazine compound of formula (I) or composition according to the invention and 5-10 wt % emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt %. Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a diamonitriazine compound of formula (I) or composition according to the invention and 1-10 wt % emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt % by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a diamonitriazine compound of formula (I) or composition according to the invention are comminuted with addition of 2-10 wt % dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt % binder (e.g. polyvinylalcohol) is added.

vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50-80 wt % of a diamonitriazine compound of formula (I) or composition according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, WS)

50-80 wt % of a compound of formula (I) or composition according to the invention are ground in a rotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodium lignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt %. Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a diamonitriazine compound of formula (I) or a composition according to the invention are comminuted with addition of 3-10 wt % dispersants (e.g. sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose) and water ad 100 wt % to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

iv) Microemulsion (ME)

5-20 wt % of a diamonitriazine compound of formula (I) or a composition according to the invention are added to 5-30 wt % organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt % surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

iv) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a diamonitriazine compound of formula (I) or a composition according to the invention, 0-40 wt % water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt % of a diamonitriazine compound of formula (I) according to the invention, 0-40 wt % water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethane-4,4′-diisocyanate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10 wt %. The wt % relate to the total CS composition.

ix) Dustable Powders (DP, DS)

1-10 wt % of a diamonitriazine compound of formula (I) or a composition according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt %.

x) Granules (GR, FG)

0.5-30 wt % of a diamonitriazine compound of formula (I) or a composition according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt %. Granulation is achieved by extrusion, spray-drying or the fluidized bed.

xi) Ultra-Low Volume Liquids (UL)

1-50 wt % of a diamonitriazine compound of formula (I) or a composition according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt %.

The agrochemical compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.

Methods for applying diamonitriazine compounds of formula (I) and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

According to one embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g. agrochemical components comprising compounds of formula (I) and/or active substances from the groups B and/or C may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

In a further embodiment, individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g. components comprising compounds of formula (I) and active substances from the groups B and/or C, can be applied jointly (e.g. after tank mix) or consecutively.

Accordingly, a first embodiment of the invention relates to compositions in the form of a agrochemical composition formulated as a 1-component composition comprising the at least one active compound of formula (I) or the at least one active compound of formula (I) (active compound A) and at least one further active compound selected from the herbicides B and the safeners C and also a solid or liquid carrier and, if appropriate, one or more surfactants.

Accordingly, a second embodiment of the invention relates to compositions in the form of a agrochemical composition formulated as a 2-component composition comprising a first formulation (component) comprising the at least one active compound A, which is a compound of formula (I), a solid or liquid carrier and, if appropriate, one or more surfactants, and a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and, if appropriate, one or more surfactants.

The active compound A, which is a compound of formula (I) and the at least one further active compound B and/or C can be formulated and applied jointly or separately, simultaneously or in succession, before, during or after the emergence of the plants. In case of separate application, the order of the application of the active compounds A, B and/or C is of minor importance. The only thing that is important is that the at least one active compound A and the at least one further active compound B and/or C are present simultaneously at the site of action, i.e. are at the same time in contact with or taken up by the plant to be controlled or to be safened.

The compounds of formula (I) or compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).

The compounds of formula (I) or compositions according to the invention control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

The compounds of formula (I) or compositions according to the invention are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha). The herbicidal compositions may also be applied by the low-volume or the ultra-low-volume method, or in the form of microgranules.

Application of the compounds of formula (I) or herbicidal compositions according to the present invention can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.

The compounds of formula (I) or herbicidal compositions according to the present invention can be applied pre- or post-emergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition of the invention, of a crop plant. If the active compounds A and B and, if appropriate C, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

In a further embodiment, the composition according to the invention can be applied by treating seed. The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula (I) according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.

The term “seed” comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.

Moreover, it may be advantageous to apply the compounds of formula (I) or compositions of the present invention on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.

When employed in plant protection, the amounts of active substances applied, i.e. A (compounds of formula (I)) and B and, if appropriate, C without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.

In another embodiment of the invention, the application rate of A (compounds of formula (I)) and B and, if appropriate, C, is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).

In another preferred embodiment of the invention, the rates of application of the compounds of formula (I) according to the present invention (total amount of compounds of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.

In another preferred embodiment of the invention, the application rates of the compounds of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.

In another preferred embodiment of the invention, the application rate of the compounds of formula (I) is 0.1 to 1000 g/ha, preferably 1 to 750 g/ha, more preferably 5 to 500 g/ha.

The required application rates of herbicidal compounds B are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.

The required application rates of safeners C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.

In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.

In another embodiment of the invention, to treat the seed, the amounts of active substances applied, i.e. A and B and, if appropriate, C are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.

When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

In the methods of the present invention it is immaterial whether the herbicide compound A of formula (I), and the further herbicide component B and/or the herbicide safener compound C are formulated and applied jointly or separately. In the case of separate application it is of minor importance, in which order the application takes place. It is only necessary, that the herbicide compound A and the herbicide compound B and/or the herbicide safener compound C are applied in a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of at most 14 days, in particular at most 7 days.

Depending on the application method in question, the compositions according to the invention can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

Preferred crops are Arachis hypogaea, Beta vulgaris spec. altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays

Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or permanent crops.

The compositions according to the invention can also be used in genetically modified plants. The term “genetically modified plants” is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species' genome or to exhibit a deletion of DNA that was native to that species' genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone. Often, a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides. e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.

Plants that have been modified by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific classes of herbicides, such as auxinic herbicides such as dicamba or 2,4-D; bleacher herbicides such as 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylureas or imidazolinones; enolpyruvyl shikimate 3-phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetylCoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering; furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxinic herbicides, or ACCase inhibitors. These herbicide resistance technologies are, for example, described in Pest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by mutagenesis and conventional methods of breeding, e. g., Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g., imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g., tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or commercially available under the brands or trade names RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e. g., VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g., Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g., WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus (corn cultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivars producing the Cry1Ac toxin), Bollgard® II (cotton cultivars producing Cry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g., Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lysozym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.g., in the publications mentioned above.

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

Furthermore, it has been found that the compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard compositions have been found for the desiccation and/or defoliation of plants, processes for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.

As desiccants, the compositions according to the invention are suitable in particular for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.

Also of economic interest is the facilitation of harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.

-   -   Another aspect of the invention is an agrochemical composition         comprising a herbicidal active amount of at least one compound         of formula (I) as defined above and at least one inert liquid         and/or solid carrier and, if appropriate, at least one         surface-active substances.     -   A further aspect of the invention is a method of controlling         undesired vegetation, which comprises allowing a herbicidally         active amount of at least one compound of formula (I) as defined         above to act on plants, their environment or on seed.     -   A further aspect of the invention in is the use of a compound of         formula (I) as defined above as a herbicide or for the         desiccation/defoliation of plants.

A further embodiment of the invention is a method of controlling undesired vegetation, which comprises allowing a herbicidally active amount of at least one compound of formula (I) and as defined above to act on plants, their environment or on seed.

The preparation of the diaminotriazine compounds of formula (I) is illustrated by examples; however, the subject matter of the present invention is not limited to the examples given.

The products shown below were characterized by the mass ([m/z]) or retention time (RT; [min.]) determined by HPLC-MS spectrometry.

HPLC-MS=high performance liquid chromatography-coupled mass spectrometry; HPLC column:

RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm; mobile phase: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA using a gradient from 5:95 to 100:0 over 5 minutes at 40° C., flow rate 1.8 ml/min.

MS: quadrupole electrospray ionization, 80 V (positive mode).

The following abbreviations are used:

TFA: Trifluoroacetic acid

CH: Cyclohexane

EtOAc: Ethyl acetate

THF: Tetrahydrofurane

MeOH: Methanol

HPLC: High pressure chromatography

LC: Liquid chromatography

MS: Mass spectrometry

A PREPARATION EXAMPLES Example 1: N4-[2-fluoro-6-[3-fluoro-5-(trifluoromethyl)phenoxy]phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine 1.1: 1-fluoro-3-[3-fluoro-5-(trifluoromethyl)phenoxy]-2-nitro-benzene

A suspension of 3-fluoro-5-(trifluoromethyl)phenol (1 g, 5.55 mmol), 1,3-difluoro-2-nitro-benzene (0.88 g, 5.55 mmol) and K2CO3 (1.53 g, 11.1 mmol) in DMF is heated to 100° C. for 6 h. Water and ethyl acetate are added and the phases separated. The organic phase is washed with water, dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. Column chromatography (ISCO-CombiFlash Rf, cyclohexane/ethyl acetate) of the crude product yields the desired product in 85% (1.50 g). HPLC: t_(1/2)=1.433 min; MS (ESI) m/z=320 [M+H⁺].

2.2: 2-fluoro-6-[3-fluoro-5-(trifluoromethyl)phenoxy]aniline

A solution of 1-fluoro-3-[3-fluoro-5-(trifluoromethyl)phenoxy]-2-nitro-benzene (1.50 g, 4.7 mmol) in acidic acid (5 mL) is added in a drop wise fashion to a suspension of zinc (1.84 g, 28.2 mmol) in acidic acid (25 mL). After the addition is complete the mixture is stirred for 5 minutes at ambient temperature and then filtered through a pad of Celite® (the filter cake is washed with MeOH). The combined filtrates are concentrated under reduced pressure and the resulting oil is dissolved in water. The aqueous phase is washed with EtOAc, brought to pH 12 with aq. NaOH (2 mol/I) and then extracted with CH₂Cl₂. The organic phase is dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. Column chromatography (ISCO-CombiFlash Rf, cyclohexane/ethyl acetate) of the crude product yields the desired product in 54% (0.73 g) yield.

HPLC: t_(1/2)=1.287 min; MS (ESI) m/z=289.8[M+H⁺].

3.3: 1-carbamimidoyl-3-[2-fluoro-6-[3-fluoro-5-(trifluoromethyl)phenoxy]phenyl]-guanidine

To a solution of 2-fluoro-6-[3-fluoro-5-(trifluoromethyl)phenoxy]aniline (0.73 g, 2.52 mmol) and 1-cyanoguanidine (0.25 g, 3.03 mmol) in acetonitrile (20 mL) aq. HCl (38% w/w, 0.45 mL) is added. The resulting suspension is heated to reflux for 3 h, cooled to ambient temperature and aq. NaOH (2 mol/L) is added until a pH of 12 is reached. Ethyl acetate is added and the phases were separated. The organic phase is dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The resulting crude product (0.9 g, 96%) is used without any further purification in the next step.

HPLC: t_(1/2)=0.908 min; MS (ESI) m/z=373.8 [M+H⁺].

4.4: N4-[2-fluoro-6-[3-fluoro-5-(trifluoromethyl)phenoxy]phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine

2-Fluoro-2-methyl-propanoyl chloride (0.29 g, 1.97 mmol) is added in a drop wise fashion to a solution of 1-carbamimidoyl-3-[2-fluoro-6-[3-fluoro-5-(trifluoromethyl)phenoxy]phenyl]guanidine (0.9 g, 2.17 mmol) in a mixture of THF (20 mL) and triethylamine (0.6 g, 2.17 mmol). The resulting reaction mixture is heated to 60° C. for 4 h, cooled to ambient temperature and diluted with water and ethyl acetate. The phases are separated and the organic phase is dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure. Column chromatography of the resulting crude product (ISCO-CombiFlash Rf, cyclohexane/ethyl acetate) yields the desired triazine as a colorless solid (0.3 g, 34% yield). HPLC: t_(1/2)=1.115 min; MS (ESI) m/z=443.9 [M+H⁺].

The compounds 2 to 103 listed below in table 4 to table 10 have been prepared by analogy to the example 1 mentioned above.

Compounds 2 to 4 are listed in table 4, wherein X are defined in table 4.

TABLE 4 MS¹⁾ no X Q [m/z] 2. CF(CH₃)₂ S 402.2 3. CF(CH₃)₂ SO₂ 434.2 4. CF(CH₃)₂ SO 418.1 ¹⁾Mass Spectrum M⁺ or [M + H]⁺ [m/z]

Compounds 5 to 41 are listed in table 5, wherein X, R^(a), R⁶, R⁷, R⁸, R⁹, R¹⁰ are defined in table 5.

TABLE 5 MS¹⁾ no. X Q R^(a) R⁶ R⁷ R⁸ R⁹ R¹⁰ [m/z] 5. CF(CH₃)₂ O F H CH₃ H CH₃ H 386.0 6. CF(CH₃)₂ O H H CH₃ H H H 354.2 7. CF(CH₃)₂ O F H CH₃ H H H 372.1 8. CF(CH₃)₂ O H H F H H H 358.2 9. CF(CH₃)₂ O H H CH₃ H CH₃ H 368.2 10. CF(CH₃)₂ O F H F H H H 376.1 11. CHFCH₃ O F H CH₃ H CH₃ H 372.1 12. CF(CH₃)₂ O F H CF₃ H CF₃ H 494.2 13. CF(CH₃)₂ O F H Cl H Cl H 426.1 14. cPent O F H CH₃ H CH₃ H 395.0 15. Cy O F H CH₃ H CH₃ H 408.7 16. C(CH₃)₃ O F H CH₃ H CH₃ H 382.7 17. CHCH₂(CH₃)₂ O F H CH₃ H CH₃ H 382.7 18. CH₂C(CH₃)₃ O F H CH₃ H CH₃ H 396.7 19. CH₂(CH₃)₂ O F H CH₃ H CH₃ H 368.0 20. CF(CH₃)₂ O F H CH₃ Cl CH₃ H 420.0 21. CF(CH₃)₂ O F H CH₃ CH₃ H H 386.0 22. CF(CH₃)₂ O F CH₃ H CH₃ H H 386.3 23. CF(CH₃)₂ O F CH₃ H H H CH₃ 386.0 24. CF(CH₃)₂ O F H F H F H 394.1 25. CF(CH₃)₂ O F H H H H H 358.2 26. CF(CH₃)₂ O F CH₃ CH₃ H H H 386.2 27. CF(CH₃)₂ O F H OCH₃ H OCH₃ H 418.2 28. CF(CH₃)₂ O F H CH₃ H Cl H 406.1 29. CF(CH₃)₂ O CH₃ H CH₃ H CH₃ H 382.2 30. CF(CH₃)₂ O F CH₃ H H CH₃ H 386.2 31. CCl(CH₃)₂ O F H CH₃ H CH₃ H 402.1 32. CF(CH₃)CH₂CH₃ O F H CH₃ H CH₃ H 400.0 33. CH(cPr)CH₃ O F H CH₃ H CH₃ H 395.0 34. CH(CH₃)cBut O F H CH₃ H CH₃ H 394.0 35. CH(CH₃)cPent O F H CH₃ H CH₃ H 408.0 36. C(CH₃)₂OCH₃ O F H CH₃ H CH₃ H 398.0 37. CF(CH₃)₂ O Cl H CH₃ H CH₃ H 402.1 38. CH(CH₃)Cy O F H CH₃ H CH₃ H 422.0 39. CH(OCH₃)CH₃ O F H CH₃ H CH₃ H 383.0 40. CF(CH₃)₂ O F H CH₃ H CH₃ H 386.0 41. CF(CH₃)₂ C F H CH₃ H CH₃ H 384.2 ¹⁾Mass Spectrum M+ or [M + H]+ [m/z]

Compounds 42 to 43 are listed in table 6, wherein X, R⁷, R⁹ are defined in table 6.

TABLE 6 MS¹⁾ no X R⁷ R⁹ [m/z] 42 CF(CH₃)₂ H H 394.1 43 CF(CH₃)₂ CH₃ CH₃ 422.1 ¹⁾Mass Spectrum M+ or [M + H]+ [m/z]

Compounds 44 to 51 are listed in table 7, wherein X, R³, R⁶, R⁸ are defined in table 7.

TABLE 7 MS¹⁾ no. X R³ R⁶ R⁸ [m/z] 44. CF(CH₃)₂ F H H 378.1 45. CF(CH₃)₂ F CH₃ H 392.1 46. CF(CH₃)₂ F OCH₃ H 408.2 47. CF(CH₃)₂ Ph H H 436.2 48. CF(CH₃)₂ F H CH₃ 392.1 49. CF(CH₃)₂ F H OCH₃ 408.1 50. CF(CH₃)₂ F H Cl 412.1 51. CF(CH₃)₂ F H CN 403.1 ¹⁾Mass Spectrum M+ or [M + H]+ [m/z]

Compounds 52 to 76 are listed in table 8, wherein X, Q, R^(a), R⁶, R⁷, R⁸, R⁹ and R¹⁰ are defined in table 8.

TABLE 8 MS¹⁾ X Q R^(a) R⁶ R⁷ R⁸ R⁹ R¹⁰ [m/z] 52. CF(CH₃)₂ O F H CF₃ H CF₃ H 494.0 53 CF(CH₃)₂ O F H F H CF₃ H 444.0 54 CF(CH₃)₂ O F H Cl H F H 410.0 55. CF(CH₃)₂ O F H Br H Br H 516.0 56. CF(CH₃)₂ O F H Br H F H 456.0 57. CF(CH₃)₂ O F H Cl H OMe H 422.0 58. CF(CH₃)₂ O F H Cl H Br H 472.0 59. CF(CH₃)₂ O F H F H CN H 401.0 60. CF(CH₃)₂ O F H Br H OCF₃ H 522.0 61. CF(CH₃)₂ O F H Br H OMe H 468.0 62. CF(CH₃)₂ O F H F H OMe H 406.0 63. CF(CH₃)₂ O F H Me H OMe H 402.0 64. CF(CH₃)₂ O F H Cl H OCF₃ H 476.0 65. CF(CH₃)₂ O F H OMe H CF₃ H 456.0 66. CF(CH₃)₂ O F H Me H CF₃ H 440.0 67. CF(CH₃)₂ O F H I H I H 610.0 68. CF(CH₃)₂ O F H OEt H OEt H 446.0 69. CF(CH₃)₂ O F H Me H OPr H 530.0 70. CF(CH₃)₂ O F H Br H O^(i)Pr H 496.0 71. CF(CH₃)₂ O F H Me H OEt H 416.0 72. CF(CH₃)₂ O F H Me H Prop-2-ynoxy H 426.0 73. CF(CH₃)₂ O F H Br H CF₃ H 506.0 74. CF(CH₃)₂ O F H Cl H CF₃ H 460.0 75. CF(CH₃)₂ O F H Me H 2-Ethoxy- H 460.0 ethoxy 76. CF(CH₃)₂ O F H Me H Allyloxy H 428.0 ¹⁾Mass Spectrum M+ or [M + H]+ [m/z]

Compound 77 is listed in table 9, wherein X, Q, R^(a), R^(b), R⁶, R⁷, R⁸, R⁹ and R¹⁰ are defined in table 9.

TABLE 9 MS¹⁾ no X Q R^(a) R^(b) R⁶ R⁷ R⁸ R⁹ R¹⁰ [m/z] 77. CF(CH₃)₂ O F F H Me H Me H 404.1 ¹⁾Mass Spectrum M+ or [M + H]+ [m/z]

Compounds 78 to 103 is listed in table 10, wherein X, Q, R^(a), R⁶, R⁷, R⁸, R⁹ and R¹⁰ are defined in table 10.

TABLE 10 MS¹⁾ no X Q R^(a) R⁶ R⁷ R⁸ R⁹ R¹⁰ [m/z] 78. CF(CH₃)₂ O F H Me H isobutoxy H 444.0 79. CF(CH₃)₂ O F H Me H 2,2-difluoro- H 452.0 ethoxy 80. CF(CH₃)₂ O F H CF₃ H dimethyl- H 469.0 amino 81. CF(CH₃)₂ O F H Me H 2,2,2- H 470.0 trifluoroethoxy 82. CF(CH₃)₂ O F H F H OCHF₂ H 442.0 83. CF(CH₃)₂ O F H Me H cyclobutyl- H 456.0 methoxy 84. CF(CH₃)₂ O F H I H OMe H 514.0 85. CF(CH₃)₂ O F H Me H cyclopentoxy H 456.0 86. CF(CH₃)₂ O F H Me H cyclohexoxy H 470.0 87. CF(CH₃)₂ O F H CF₃ H Ph H 502.0 88. CF(CH₃)₂ O F H CF₃ H H H 426.0 89. CF(CH₃)₂ O F H i-Pr H H H 400.0 90. CF(CH₃)₂ O F H Et H H H 386.0 91. CF(CH₃)₂ O F H methoxy- H H H 416.0 carbonyl 92. CF(CH₃)₂ O F H t-Bu H H H 414.0 93. CF(CH₃)₂ O F H Br H H H 438.0 94. CF(CH₃)₂ O F H Cl H H H 392.0 95. CF(CH₃)₂ O F H OCHF₂ H H H 424.0 96. 1-fluoro- O F H Me H Me H 412.0 cyclopentyl 97. CF(CH₃)₂ O F H OCF₃ H H H 424.1 98. CF(CH₃)₂ O F H OCF₃ H Ph H 518.0 99. CF(CH₃)₂ O F H Isopropoxy H F H 434.0 100. CF(CH₃)₂ O CN H Me H Me H 393.0 101. CF(CH₃)₂ O F H I H F H 502.0 102. CF(CH₃)₂ NMe F H H H H H 371.1 103. CF(CH₃)₂ NMe F H Me H H H 385.0 ¹⁾Mass Spectrum M+ or [M + H]+ [m/z]

Compounds 104 to 114 is listed in table 11, wherein X, Q, R^(a), R⁷ and R⁹ are defined in table 11.

TABLE 11 MS¹⁾ no X Q R¹ R² R^(a) R⁷ R⁹ [m/z] 104. CF(CH₃)₂ O H CH₃ F CH₃ CH₃ 400.0 105. CF(CH₃)₂ O CH₃ H F CH₃ CH₃ 400.0 106. CF(CH₃)₂ O C(═O)CH₃ C(═O)CH₃ F CH₃ CH₃ 470.0 107. CF(CH₃)₂ O CH₃ CH₃ F CH₃ CH₃ 414.0 108. CF(CH₃)₂ O C(═O)CH₃ CH₃ F CH₃ CH₃ 442.0 109. 1-fluorocyclopentyl O H H F Cl Cl 452.0 110. 1-fluorocyclopentyl O H H Cl CH₃ CH₃ 428.0 111. CF(CH₃)₂ O C(═O)CH₃ H F CH₃ CH₃ 428.0 112. 1-cyclopropyl-1- O H H F CH₃ CH₃ 412.0 fluoro-ethyl 113. CF(CH₃)₂ O H C(═O)CH₃ F CH₃ CH₃ 428.0 114. CF(CH₃)₂ O H CH₃ F CH₃ CH₃ 400.0 ¹⁾Mass Spectrum M+ or [M + H]+ [m/z]

ABBREVIATION

cPr Cyclopropyl cBut Cyclobutyl cPent cyclopentyl Cy Cyclohexyl Ph phenyl

B USE EXAMPLES

The herbicidal activity of the azines of formula (I) was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 278 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C., respectively.

The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A moderate herbicidal activity is given at values of at least 60, a good herbicidal activity is given at values of at least 70, and a very good herbicidal activity is given at values of at least 85.

The plants used in the greenhouse experiments were of the following species:

Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AMARE Amaranthus retroflexus APESV Apera spica-venti ECHCG Echinocloa crus-galli LAMPU Lamium purpureum POLCO Polygonum convolvulus SETFA Setaria faberi SETVI Setaria viridis STEME Stellaria media VIOAR Viola arvensis CAPBP Capsella bursa-pastoris PHBPU Pharbitis purpurea ELEIN Eleusine indica

Example 5 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against ABUTH, ECHCG and SETFA.

Example 7 applied by pre-emergence method at an application rate of 0.5 kg/ha, showed good to very good herbicidal activity against ABUTH, AMARE and ECHCG.

Example 10 applied by pre-emergence method at an application rate of 0.5 kg/ha, showed very good herbicidal activity against AMARE, APESV and ECHCG.

Example 11 applied by pre-emergence method at an application rate of 0.125 kg/ha, showed very good herbicidal activity against ABUTH, ECHCG and SETFA.

Example 12 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against AMARE, APESV and SETFA.

Example 13 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against AMARE, APESV and SETFA.

Example 19 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against APESV, ECHCG and SETFA.

Example 24 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against ABUTH, APESV and ECHCG.

Example 25 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against ALOMY, AMARE and APESV.

Example 27 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against APESV, ECHCG and SETFA.

Example 28 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against ABUTH, APESV and SETFA.

Example 32 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against APESV, ECHCG and SETFA.

Example 36 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very good herbicidal activity against APESV and good herbicidal activity against ALOMY.

Example 37 applied by pre-emergence method at an application rate of 0.25 kg/ha, showed very APESV and good herbicidal activity against ECHCG.

Example 42 applied by pre-emergence method at an application rate of 0.5 kg/ha, showed good to very good herbicidal activity against ABUTH, AMARE and ECHCG.

Example 43 applied by pre-emergence method at an application rate of 0.5 kg/ha, showed good to very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 44 applied by pre-emergence method at an application rate of 0.5 kg/ha, showed good to very good herbicidal activity against AMARE and good herbicidal activity against SETFA.

Example 50 applied by pre-emergence method at an application rate of 0.5 kg/ha, showed good to very good herbicidal activity against AMARE and good herbicidal activity against ABUTH.

Example 50 applied by pre-emergence method at an application rate of 0.5 kg/ha, showed good to very good herbicidal activity against ABUTH and good herbicidal activity against AMARE.

Example 52 applied by post-emergence method at an application rate of 63 g/ha, showed very good herbicidal activity against CAPBP, SETVI and STEME.

Example 53 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 54 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 55 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 56 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against AMARE and SETFA and showed good herbicidal activity against ABUTH.

Example 57 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 58 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 59 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 60 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 61 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 62 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, AMARE and SETFA.

Example 63 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ECHCG, AMARE and SETFA.

Example 64 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ELEIN, PHBPU and SETFA.

Example 65 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, ECHCG and SETFA.

Example 67 applied by post-emergence method at an application rate of 125 g/ha, showed good herbicidal activity against ECHCG and SETFA.

Example 68 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ABUTH, ECHCG and SETFA.

Example 69 applied by post-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ECHCG and SETFA.

Example 80 applied by pre-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against ECHCG and SETFA.

Example 81 applied by pre-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against AMARA and SETFA and showed good herbicidal activity against ABUTH.

Example 82 applied by pre-emergence method at an application rate of 125 g/ha, showed very good herbicidal activity against AMARA, ABUTH and SETFA.

Example 83 applied by pre-emergence method at an application rate of 250 g/ha, showed very good herbicidal activity against AMARA and showed good herbicidal activity against APESV and ECHCG.

Example 84 applied by pre-emergence method at an application rate of 250 g/ha, showed very good herbicidal activity against AMARA, ECHCG and SETFA.

Example 85 applied by pre-emergence method at an application rate of 250 g/ha, showed very good herbicidal activity against AMARA.

Example 86 applied by pre-emergence method at an application rate of 500 g/ha, showed good herbicidal activity against SEFTA.

Example 87 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against AMARA, ECHCG and SETFA.

Example 88 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against AMARA, ECHCG and SETFA.

Example 89 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against APESV, ECHCG and ABUTH.

Example 90 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against APESV, ECHCG and AMARE.

Example 91 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against APESV.

Example 92 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against APESV, ECHCG and SETFA.

Example 93 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against APESV, ECHCG and SETFA.

Example 94 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against APESV, ECHCG and SETFA.

Example 95 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against APESV, ECHCG and SETFA.

Example 96 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against ABUTH, ECHCG and SETFA.

Example 97 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against ABUTH, ECHCG and SETFA.

Example 98 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against AMARE, ECHCG and SETFA.

Example 99 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against AMARE, ECHCG and ALOMY.

Example 100 applied by pre-emergence method at an application rate of 250 g/ha, showed very good herbicidal activity against APESV and ECHCG and showed good herbicidal activity against ABUTH.

Example 101 applied by pre-emergence method at an application rate of 250 g/ha, showed very good herbicidal activity against SEFTA and ECHCG and showed good herbicidal activity against ALOMY.

Example 102 applied by pre-emergence method at an application rate of 1000 g/ha, showed very good herbicidal activity against AMARE, SEFTA and ECHCG.

Example 103 applied by pre-emergence method at an application rate of 500 g/ha, showed very good herbicidal activity against AMARE, SEFTA and ECHCG.

Example 2 applied by pre-emergence method at an application rate of 1000 g/ha, showed good herbicidal activity against ABUTH.

Example 15 applied by pre-emergence method at an application rate of 1000 g/ha, showed very good herbicidal activity against ABUTH.

Example 16 applied by pre-emergence method at an application rate of 2000 g/ha, showed very good herbicidal activity against AMARE, ABUTH and APESV.

Example 17 applied by pre-emergence method at an application rate of 1000 g/ha, showed very good herbicidal activity against SEFTA and showed good herbicidal activity against APESV.

Example 19 applied by pre-emergence method at an application rate of 250 g/ha, showed very good herbicidal activity against SEFTA, ECHCG and APESV.

Example 34 applied by pre-emergence method at an application rate of 1000 g/ha, showed very good herbicidal activity against SEFTA, ECHCG and APESV.

Example 36 applied by pre-emergence method at an application rate of 1000 g/ha, showed very good herbicidal activity against SEFTA, ECHCG and APESV.

Example 39 applied by pre-emergence method at an application rate of 1000 g/ha, showed very good herbicidal activity against ABUTH and APESV.

The respective stated components A and B, and if appropriate, C were formulated as a 10% by weight strength emulsion concentrate and, with addition of the amount of solvent system, introduced into the spray liquor used for applying the active compound. In the examples, the solvent used was water.

In the examples below, using the method of S. R. Colby (1967) “Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds 278, p. 22ff., the value E, which is expected if the activity of the individual active compounds is only additive, was calculated. E=X+Y−(X·Y/100) where X=percent activity using active compound A at an application rate a; Y=percent activity using active compound B at an application rate b; E=expected activity (in %) by A+B at application rates a+b.

If the value found experimentally is higher than the value E calculated according to Colby, a synergistic effect is present.

The plants used in the greenhouse experiments were of the following species:

Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopercurus myosuroides AMARE Amaranthus retroflexus AMBEL Ambrosia artemisiifolia APESV Apera spica-venti BIDPI Bidens pilosa BRADE Brachiaria deflexa BRAPL Brachiaria plantaginea CHEAL Chenopodium album COMBE Commenline benghalensis DIGSA Digitaria sanguinales ECHCG Echinocloa crus-galli ELEIN Eleusine indica ERBVI Eriochloa villosa ERICA Erigeron canadensis LAMAM Lamium amplexicaule LAMPU Lamium purpureum PANDI Panicum dichotomiflorun PHBPU Pharbitis purpurea POAAN Poa annua POLCO Polygonum convolvulus SETLU Setaria lutescens SETFA Setaria faberi SETVE Setaria verticillata SETVI Setaria viridis SOLNI Solanum nigrum SORHA Sorghum halepense STEME Stellaria media VERPE Veronica persica

The results of these tests are given below in the use examples and demonstrate the synergistic effect of the mixtures comprising at least one compound of the formula (I) and at least one herbicide B. In this context, a.s. means active substance, based on 100% active ingredient. 

The invention claimed is:
 1. A diaminotriazine compound of formula (I)

wherein p is 1 or 2; q is 0, 1, 2 or 3 provided that p+q is 1, 2, 3 or 4; Q is a chemical bond, O, S(O)_(m), CR^(q1)R^(q2), NR^(q3), C(O), C(O)O, CR^(q1)R^(q2)—O, S(O)_(m)NR^(q3) or C(O)NR^(q3), wherein m is 0, 1 or 2; R^(q1), R^(q2) are hydrogen, halogen or C₁-C₄-alkyl; R^(q3) is H, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, where the aliphatic parts of the 6 aforementioned radicals are unsubstituted, partly or completely halogenated; Ar is phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R^(A) which are selected from the group consisting of halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl, C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino, (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl, (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the aliphatic and cycloaliphatic parts of the 22 aforementioned radicals are unsubstituted, partly or completely halogenated and where the cycloaliphatic parts of the last 4 mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups, phenyl, phenyl-C₁-C₆-alkyl, phenylsulfonyl, phenylaminosulfonyl, phenylaminocarbonyl, phenyl(C₁-C₆-alkyl)aminocarbonyl, phenylcarbonyl and phenoxycarbonyl, wherein phenyl in the last 8 mentioned radicals are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, it being possible that R^(A) are identical or different; R^(a) is selected from the group consisting of hydrogen, halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino, (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl, (C₁-C₆-alkyl)-carbonyloxy, where the aliphatic and cycloaliphatic parts of the 14 aforementioned radicals are unsubstituted, partly or completely halogenated; R^(b) is selected from the group consisting of halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl, C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino, (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl, (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the aliphatic and cycloaliphatic parts of the 22 aforementioned radicals are unsubstituted, partly or completely halogenated and where the cycloaliphatic parts of the last 4 mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups, for q=2 or 3 it being possible that R^(b) are identical or different; R¹ is selected from the group consisting of H, OH, S(O)₂NH₂, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where the aliphatic and cycloaliphatic parts of the 15 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenyl-C₁-C₆-alkyl, phenylsulfonyl, phenylaminosulfonyl, phenylaminocarbonyl, phenyl(C₁-C₆-alkyl)aminocarbonyl, phenylcarbonyl and phenoxycarbonyl, wherein phenyl in the last 8 mentioned radicals are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; R² is selected from the group consisting of H, OH, S(O)₂NH₂, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₃-C₆-cycloalkyl)-carbonyl C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where the aliphatic and cycloaliphatic parts of the 15 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenylsulfonyl, phenylaminosulfonyl, phenylaminocarbonyl, phenyl(C₁-C₆-alkyl)aminocarbonyl, phenyl-C₁-C₆ alkyl, phenoxy, phenylcarbonyl and phenoxycarbonyl, wherein phenyl in the last 9 mentioned radicals is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; X is a radical selected from the group consisting of CR³R⁴R⁵, phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R^(Ar) which are identical or different; NR^(3a)R^(3b) OR³ and S(O)_(k)R^(3d) with k being 0, 1 or 2 wherein R³ is selected from the group consisting of H, halogen, OH, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the aliphatic and cycloaliphatic parts of the 9 aforementioned radicals are unsubstituted, partly or completely halogenated; R⁴ is selected from the group consisting of H, halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; R⁵ is selected from the group consisting of halogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, C₃-C₆-cycloalkenyl and C₁-C₆-alkoxy-C₁-C₆-alkyl, where the aliphatic and cycloaliphatic parts of the 7 aforementioned radicals are unsubstituted, partly or completely halogenated; R⁴ and R⁵ together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, three- to six-membered saturated or partially unsaturated heterocyclyl, and the moiety >C═CR^(x)R^(y), where R^(x) and R^(y) are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R^(Ar) selected from the group consisting of halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl, C₁-C₆-alkylthio, (C₁-C₆-alkyl)sulfinyl, (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkyl)amino, di(C₁-C₆-alkyl)amino, (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)-carbonyl, (C₁-C₆-alkyl)-carbonyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy, where the aliphatic and cycloaliphatic parts of the 22 aforementioned radicals are unsubstituted, partly or completely halogenated and where the cycloaliphatic parts of the last 4 mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups, R^(3a), R^(3b), R^(3c) or R^(3d) are independently of one another are selected from the group consisting of H, CN, S(O)₂NH₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, (C₃-C₆-cycloalkyl)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl, (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where the aliphatic and cycloaliphatic parts of the 15 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenylsulfonyl, phenyl-C₁-C₆ alkyl, phenylaminosulfonyl, phenylcarbonyl and phenoxycarbonyl, wherein phenyl in the last 6 mentioned radicals is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, or R^(3a), R^(3b) together with the nitrogen atom, to which they are bound, form an N-bound, mono- or bicyclic heterocyclic radical, which may have 1, 2, 3 or 4 further heteroatoms which are selected from N, O and S, which is unsubstituted or substituted by one or more identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, one of R^(3a), R^(3b) may also be OH, C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)-C₁-C₄-alkoxy C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, where the aliphatic and cycloaliphatic parts of the 7 aforementioned radicals are unsubstituted, partly or completely halogenated, or phenoxy, which is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; or an agriculturally acceptable salt; except for the following compounds: N4-[2-(3,5-dimethylphenoxy)-6-fluoro-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine, N4-[2-(3-methylphenoxy)-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine, N4-[2-(3-methylphenoxy)-6-fluoro-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine, and N4-[2-(3-fluorophenoxy)-phenyl]-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine.
 2. The compound of claim 1, wherein R^(a) is selected from the group consisting of halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, in particular from fluorine chlorine or CN.
 3. The compound of claim 1, wherein R^(b) is selected from the group consisting of and halogen, CN, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy and is in particular fluorine.
 4. The compound of claim 1, wherein the moiety

is represented by one of the following moieties A or B

wherein R^(b1), R^(b2) and R^(b3) are identical or different and are hydrogen or have one of the meanings of R^(b).
 5. The compound of claim 4, wherein R^(b1), R^(b2) and R^(b3) are selected from the group consisting of and hydrogen and fluorine.
 6. The compound of claim 1, wherein Q is selected from the group consisting of a chemical bond, O, CH₂, S, S(O) and S(O)₂.
 7. The compound of claim 1, wherein Q is NR^(q3), wherein R^(q3) is selected from H, CN and C₁-C₆-alkyl.
 8. The compound of claim 1, wherein Ar is phenyl, which carries 1 or 2 radicals R^(A).
 9. The compound of claim 1, wherein R^(A), if present, is selected from the group consisting of halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.
 10. The compound of claim 1, wherein the moiety Ar-Q is selected from the group consisting of phenyl, 4-methoxyphenyl, 4-cyanophenyl, 3-methylphenyl, 3,5-dimethylphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,5-dibromophenyl, 3,5-dimethoxyphenyl, 3,5-diethoxyphenyl, 3,5-Bis-(trifluoromethoxy)phenyl, 3,5-Bis-(trifluoromethyl)phenyl, 3,5-dicyanophenyl, 3-fluoro-5-methylphenyl, 3-chloro-5-methylphenyl, 3-bromo-5-methylphenyl, 3-methoxy-5-methylphenyl, 3-ethoxy-5-methylphenyl, 3-(trifluoromethoxy)-5-methylphenyl, 3-(trifluoromethyl)-5-methylphenyl, 3-(tert.-butyl)-5-methylphenyl, 3-cyano-5-methylphenyl, 3-chloro-5-fluorophenyl, 3-bromo-5-fluorophenyl, 3-fluoro-5-methoxyphenyl, 3-fluoro-5-ethoxyphenyl, 3-fluoro-5-(trifluoromethoxy)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 3-fluoro-5-(tert-butyl)phenyl, 3-fluoro-5-cyanophenyl, 3-chloro-5-methoxyphenyl, 3-chloro-5-ethoxyphenyl, 3-chloro-5-(trifluoromethoxy)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-chloro-5-(tert-butyl)phenyl, 3-chloro-5-cyanophenyl, 3-bromo-5-methoxyphenyl, 3-bromo-5-ethoxyphenyl, 3-bromo-5-(trifluoromethoxy)phenyl, 3-bromo-5-(trifluoromethyl)phenyl, 3-bromo-5-(tert-butyl)phenyl, 3-bromo-5-cyanophenyl, 3-ethoxy-5-methoxyphenyl, 3-(trifluoromethoxy)-5-methoxyphenyl, 3-methoxy-5-(trifluoromethyl)phenyl, 5-cyano-3-methoxyphenyl, 5-(tert-butyl)-3-methoxyphenyl, 3-(trifluoromethoxy)-5-ethoxyphenyl, 3-ethoxy-5-(trifluoromethyl)phenyl, 5-cyano-3-ethoxyphenyl, 5-(tert-butyl)-3-ethoxyphenyl, 3-(trifluoromethoxy)-5-(trifluoromethyl)phenyl, 3-(trifluoromethoxy)-5-(tert.-butyl)phenyl, 3-(trifluoromethoxy)-5-cyanophenyl, 3-(trifluoromethyl)-5-(tert.-butyl)phenyl, 3-(trifluoromethyl)-5-cyanophenyl, 3-cyano-5-(tert.-butyl)phenyl and 3,5-bis(tert.-butyl)phenyl.
 11. The compound of claim 1, wherein the moiety Ar-Q is selected from the group consisting of 3,5-bis(trifluoromethyl)phenoxy, 3-fluoro-5-(trifluoromethyl)phenoxy, 3-chloro-5-fluoro-phenoxy, 3,5-bis(bromo)phenoxy, 3-bromo-5-fluoro-phenoxy, 3-chloro-5-(methoxy)phenoxy, 3-chloro-5-bromo-phenoxy, 3-fluoro-5-cyano-phenoxy, 3-bromo-5-trifluormethoxy-phenoxy, 3-bromo-5-methoxy-phenoxy, 3-fluoro-5-methoxy-phenoxy, 3-methyl-5-methoxy-phenoxy, 3-chloro-5-trifluormethoxy-phenoxy, 3-trifluormethoxy-5-trifluomethyl-phenoxy, 3-methyl-5-trifluormethyl-phenoxy, 3-iodo-5-iodo-phenoxy, 3-ethoxy-5-ethoxy-phenoxy, 3-methyl-5-propoxy-phenoxy, 3-bromo-5-isopropoxy-phenoxy, 3-methyl-5-ethoxy-phenoxy, 3-methyl-5-(prop-2-ynoxy)-phenoxy, 3-bromo-5-trifluormethyl-phenoxy, 3-chloro-5-trifluormethyl-phenoxy, 3-methyl-5-(2-ethoxyethoxy)-phenoxy, 3-methyl-5-allyloxy-phenoxy, 3-methyl-5-methyl-phenoxy, 3-methyl-5-isobutoxy-phenoxy, 3-methyl-5-(2,2-difluoroethoxy)-phenoxy, 3-methyl-5-dimethylamino-phenoxy, 3-methyl-5-(2,2,2-trifluoroethoxy)-phenoxy, 3-fluoro-5-difluoromethoxy-phenoxy, 3-methyl-5-(cyclobutylmethoxy)-phenoxy, 3-iodo-5-methoxy-phenoxy, 3-methyl-5-cyclopentoxy-phenoxy, 3-methyl-5-cyclohexoxy-phenoxy, 3-trifluoromethyl-5-phenyl-phenoxy, 3-trifluoromethyl-phenoxy, 3-isopropoxy-phenoxy, 3-ethyl-phenoxy, 3-methoxycarbonyl-phenoxy, 3-tert-butyl-phenoxy, 3-bromo-phenoxy, 3-chloro-phenoxy, 3-difluoromethoxy-phenoxy, 3-iodo-5-methoxy-phenoxy, 3-trifluormethoxy-phenoxy, 3-difluoromethoxy-5-phenyl-phenoxy, 3-isopropoxy-5-fluoro-phenoxy, 3-iodo-5-fluoro-phenoxy, N-methyl-N-phenyl-amine and N-methyl-N-(m-tolyl)-amine, 3-methyl-phenoxy, 3-fluoro-phenoxy, 3-chloro-5-chloro-phenoxy, 3,5-dimethyl-4-chloro-phenoxy, 3,4-dimethyl-phenoxy, 2,4-dimethyl-phenoxy, 2-methyl-phenoxy, 3-flouro-5-fluoro-phenoxy, phenoxy, 2,3-dimethyl-phenoxy, 3,5-diethoxy-phenoxy, 3-methyl-5-chloro-phenoxy, 2,5-dimethyl-phenoxy, 2,6-dimethyl-phenoxy, 3-methoxy-phenyl, 4-methyl-phenyl, 4-methoxy-phenyl, 4-chloro-phenyl, 4-cyano-phenyl.
 12. The compound of claim 1, wherein R¹ is selected from the group consisting of H, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl, (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-alkyl)sulfonyl, C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl, where the aliphatic parts of the 11 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenylcarbonyl and phenyl-C₁-C₆ alkyl, wherein phenyl in the last 3 mentioned radical is unsubstituted or substituted by 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.
 13. The compound of claim 1, wherein R² is selected from the group consisting of H, CN, C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkyl)sulfonyl, (C₁-C₆-alkoxy)carbonyl, (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl, where the aliphatic parts of the 10 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenylcarbonyl and C₁-C₆ alkylphenyl, wherein phenyl in the last 3 mentioned radical is unsubstituted or substituted by 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-alkoxy.
 14. The compound of claim 1, wherein X is a radical CR³R⁴R⁵.
 15. The compound of claim 14, wherein R³ is selected from the group consisting of hydrogen, fluorine, chlorine, C₁-C₄-alkyl and C₁-C₄-alkoxy; R⁴ is selected from the group consisting of hydrogen, fluorine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₆-haloalkoxy; R⁵ is selected from the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, and C₁-C₆-alkoxy-C₁-C₆-alkyl; or R⁴ and R⁵ together with the carbon atom to which they are attached form a moiety selected from the group consisting of C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl and three- to six-membered saturated or partially unsaturated heterocyclyl.
 16. The compound of claim 1, wherein X is phenyl, which carries 1, 2, 3, 4 or 5 radicals R^(Ar), wherein R^(Ar) is halogen, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, (C₃-C₆-cycloalkyl)methoxy, C₂-C₆-alkynyl, C₂-C₆-alkenyl, C₂-C₆-alkynyloxy and C₂-C₆-alkenyloxy.
 17. The compound of claim 16, wherein R^(Ar) is selected from the group consisting of F, Cl, CN, CF₃, methyl, vinyl, ethynyl, cyclopropyl, methoxy, ethoxy, isopropyloxy, allyloxy, propargyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, (cycloproyl)methoxy and 2-butyloxy.
 18. The compound of claim 1, wherein X is NR^(3a)R^(3b), wherein R^(3a) R^(3b) are independently of one another H, CN, S(O)₂NH₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkyl)-carbonyl, (C₃-C₆-cycloalkyl)-carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)sulfonyl, C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl and (C₁-C₆-alkoxy)sulfonyl, where the aliphatic parts of the 15 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenylsulfonyl or phenyl-C₁-C₆ alkyl, wherein phenyl in the last 3 mentioned radicals is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, one of R^(3a), R^(3b) may also be OH, C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, where the aliphatic and cycloaliphatic parts of the 3 aforementioned radicals are unsubstituted, partly or completely halogenated, or R^(3a), R^(3b) together with the nitrogen atom, to which they are bound, form an N-bound saturated or unsaturated mono- or bicyclic heterocyclic radical, which may have 1, 2, 3 or 4 further heteroatoms which are selected from N, O and S, which is substituted or unsubstituted by one or more identical or different substituents selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl and C₁-C₆-haloalkoxy.
 19. An agrochemical composition comprising a herbicidal active amount of at least one compound as claimed in claim 1 and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substances.
 20. A method for the desiccation or defoliation of crop plants or for controlling undesired vegetation comprising allowing a herbicidally active amount of a compound of claim 1 to act on plants, their environment or on seed. 